US20230209847A1 - Organic light emitting element - Google Patents

Organic light emitting element Download PDF

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US20230209847A1
US20230209847A1 US17/999,979 US202117999979A US2023209847A1 US 20230209847 A1 US20230209847 A1 US 20230209847A1 US 202117999979 A US202117999979 A US 202117999979A US 2023209847 A1 US2023209847 A1 US 2023209847A1
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Hayato Kakizoe
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Kyulux Inc
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Definitions

  • the present invention relates to an organic light emitting device using a delayed fluorescent material.
  • organic light-emitting devices such as organic electroluminescent devices (organic EL devices) are being made actively.
  • various kinds of efforts have been made for increasing light emission efficiency by newly developing and combining an electron transporting material, a hole transporting material, a host material and a light emitting material to constitute an organic electroluminescent device.
  • studies relating to an organic light emitting device that utilizes a delayed fluorescent material are seen.
  • a delayed fluorescent material is a material which, in an excited state, after having undergone reverse intersystem crossing from an excited triplet state to an excited singlet state, emits fluorescence when returning back from the excited singlet state to a ground state thereof. Fluorescence through the route is observed later than fluorescence from the excited singlet state directly occurring from the ground state (ordinary fluorescence), and is therefore referred to as delayed fluorescence.
  • the occurring probability of the excited singlet state to the excited triplet state is statistically 25%/75%, and therefore improvement of light emission efficiency by the fluorescence alone from the directly occurring excited singlet state is limited.
  • a delayed fluorescent material not only the excited singlet state thereof but also the excited triplet state can be utilized for fluorescent emission through the route via the above-mentioned reverse intersystem crossing, and therefore as compared with an ordinary fluorescent material, a delayed fluorescent material can realize a higher emission efficiency.
  • a delayed fluorescent material there has been proposed a benzene derivative having a heteroaryl group such as a carbazolyl group or a diphenylamino group, and at least two cyano groups, and it has been confirmed that an organic EL device using the benzene derivative in a light emitting layer provides a high emission efficiency (see PTL 1).
  • NPL 1 reports that a carbazolyldicyanobenzene derivative (4CzTPN) is a thermally activated delayed fluorescent material and that an organic electroluminescent device using the carbazolyldicyanobenzene derivative attained a high internal EL quantum efficiency.
  • PTL 1, PTL 2 and NPL 1 report that an organic electroluminescent device using a delayed fluorescent material attained a high emission efficiency.
  • the present inventors produced organic electroluminescence devices according to the descriptions of PTL 1 and PTL 2, it was found that it was difficult to secure a sufficient lifetime. In addition, it was also found that it was difficult to realize light emission with high color purity at a short wavelength.
  • the present inventors have promoted assiduous studies for the purpose of realizing a long lifetime and a high color purity in an organic light emitting device using a delayed fluorescent material.
  • the present inventors have found that long-life light emission with high color purity can be realized by adding a plurality of delayed fluorescent materials, host materials, and light emitting materials that satisfy specific requirements to a light emitting layer.
  • the present invention has been proposed on the basis of such findings, and specifically has the following constitution.
  • An organic light emitting device having a light emitting layer that contains a first organic compound, a second organic compound, a third organic compound and a fourth organic compound satisfying the following requirements (a) to (e), wherein:
  • the second organic compound and the third organic compound are delayed fluorescent materials each having a different structure
  • the maximum component of light emission from the organic light emitting device is light emission from the fourth organic compound:
  • E S1 (1) represents a lowest excited singlet energy of the first organic compound
  • E S1 (2) represents a lowest excited singlet energy of the second organic compound
  • E S1 (3) represents a lowest excited singlet energy of the third organic compound
  • E S1 (4) represents a lowest excited singlet energy of the fourth organic compound
  • E T1 (1) represents a lowest excited triplet energy of the first organic compound
  • E T1 (2) represents a lowest excited triplet energy of the second organic compound
  • E T1 (3) represents a lowest excited triplet energy of the third organic compound
  • Conc(1) represents a concentration of the first organic compound in the light emitting layer
  • Conc(2) represents a concentration of the second organic compound in the light emitting layer
  • Conc(3) represents a concentration of the third organic compound in the light emitting layer.
  • E T1 (4) represents a lowest excited triplet energy of the fourth organic compound.
  • Conc(4) represents a concentration of the fourth organic compound in the light emitting layer.
  • the organic light emitting device is composed of a compound alone formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, a boron atom, an oxygen atom and a sulfur atom.
  • the first organic compound, the second organic compound and the third organic compound each are independently a compound formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom and a nitrogen atom.
  • the organic light emitting device of the present invention can realize long-life light emission with a high color purity.
  • FIG. 1 This is a schematic cross-sectional view showing a layer configuration example of an organic electroluminescent device.
  • FIG. 2 This is a graph showing a time-dependent change of a light emission intensity and a driving voltage of organic electroluminescent devices.
  • a numerical range expressed as “to” means a range that includes the numerical values described before and after “to” as the upper limit and the lower limit.
  • XXX is composed of means that XXX is formed of only those described after “composed of” and does not contain any others.
  • the hydrogen atom that is present in the molecule of the compound used in the invention is not particularly limited in isotope species, and for example, all the hydrogen atoms in the molecule may be 1 H, and all or a part of them may be 2 H (deuterium D).
  • the organic light emitting device of the present invention has a light emitting layer that contains a first organic compound, a second organic compound, a third organic compound and a fourth organic compound.
  • the second organic compound and the third organic compound are delayed fluorescent materials differing from each other in the structure.
  • the organic compounds satisfy, the following requirements (a) to (e):
  • E S1 (1) represents a lowest excited singlet energy of the first organic compound
  • E S1 (2) represents a lowest excited singlet energy of the second organic compound
  • E S1 (3) represents a lowest excited singlet energy of the third organic compound
  • E S1 (4) represents a lowest excited singlet energy of the fourth organic compound.
  • eV is employed as the unit.
  • E T1 (1) represents a lowest excited triplet energy of the first organic compound
  • E T1 (2) represents a lowest excited triplet energy of the second organic compound
  • E T1 (3) represents a lowest excited triplet energy of the third organic compound
  • E T1 (4) represents a lowest excited triplet energy of the fourth organic compound.
  • eV is employed as the unit.
  • Conc(1) represents a concentration of the first organic compound in the light emitting layer
  • Conc(2) represents a concentration of the second organic compound in the light emitting layer
  • Conc(3) represents a concentration of the third organic compound in the light emitting layer
  • Conc(4) represents a concentration of the fourth organic compound in the light emitting layer.
  • wt % is employed as the unit.
  • the organic light emitting device of the present invention satisfies the requirement (a) and the requirement (b) at the same time for the lowest excited singlet energy. Therefore, the lowest excited singlet energy E S1 (2), E S1 (3), and E S1 (4) of the second organic compound, the third organic compound and the fourth organic compound are all within a range of 0.3 eV or less.
  • E S1 (2) ⁇ E S1 (3) can be within a range of 0.27 eV or less, or can be within a range of 0.24 eV or less, or can be within a range of 0.20 eV or less.
  • E S1 (4) can be near to any of E S1 (2) and E S1 (3), and for example, a compound whose E S1 (4) is nearer to E S1 (2) than E S1 (3) can be selected here.
  • E S1 (2) ⁇ E S1 (4) and E S1 (4) ⁇ E S1 (3) can be both within a range of 0.25 eV or less, or can be within a range of 0.20 eV or less, or can be within a range of 0.15 eV or less. Also so far as within a range of less than 0.29 eV, they can be within a range of 0.01 eV or more, or can be within a range of 0.05 eV or more, or can be within a range of 0.10 eV or more.
  • E S1 (1) ⁇ E S1 (2) can be within a range of 0.2 eV or more, or can be within a range of 0.4 eV or more, or can be within a range of 0.6 eV or more, or also can be within a range of 1.5 eV or less, or can be within a range of 1.2 eV or less, or can be within a range of 0.8 eV or less.
  • the organic light emitting device of the present invention satisfies a relationship of the requirement (c) for the lowest excited triplet energy, and more preferably also satisfies the following requirement (c1).
  • E T1 (4) ⁇ E T1 (3) can be within a range of 0.01 eV or more, or can be within a range of 0.03 eV or more, or can be within a range of 0.05 eV or more, and also can be within a range of 0.3 eV or less, or can be within a range of 0.2 eV or less, or can be within a range of 0.1 eV or less.
  • E T1 (2) ⁇ E T1 (4) can be within a range of 0.01 eV or more, or can be within a range of 0.05 eV or more, and also can be within a range of 0.3 eV or less, or can be within a range of 0.2 eV or less.
  • E T1 (1) ⁇ E T1 (2) can be within a range of 0.2 eV or more, or can be within a range of 0.4 eV or more, and also can be within a range of 0.8 eV or less, or can be within a range of 0.6 eV or less.
  • the organic light emitting device of the present invention satisfies the requirement (d) and the requirement (e) in point of the concentration of the organic compound in the light emitting layer.
  • the organic light emitting device of the present invention further satisfies the following requirement (d1).
  • Conc(1) is preferably 30% by weight or more, and can be within a range of 50% by weight or more, or can be within a range of 65% by weight or more, and also can be within a range of 99% by weight or less, or can be within a range of 85% by weight or less, or can be within a range of 75% by weight or less.
  • Conc(2) is preferably 10% by weight or more, and can be within a range of 20% by weight or more, or can be within a range of 30% by weight or more, and also can be within a range of 45% by weight or less, or can be within a range of 40% by weight or less, or can be within a range of 35% by weight or less.
  • Conc(3) needs to fall within a range of 20% by weight or less, and is preferably 15% by weight or less, more preferably 10% by weight or less.
  • Conc(3) can be within a range of 7% by weight or less, or can also be within a range of 0.5% by weight or more, or can be within a range of 1.0% by weight or more, or can be within a range of 2% by weight or more, or can be within a range of 4% by weight or more.
  • Conc(4) is preferably 5% by weight or less, more preferably 3% by weight or less. Conc(4) can be within a range of 1% by weight or less, or can be within a range of 0.5% by weight or less, and also can be within a range of 0.01% by weight or more, or can be within a range of 0.1% by weight or more, or can be within a range of 0.3% by weight or more.
  • the organic light emitting device of the present invention further satisfies the following requirement (f).
  • Conc(3)/Conc(4) can be within a range of 7 or more, or can be within a range of 9 or more, and also can be within a range of 500 or less, or can be within a range of 100 or less, or can be within a range of 50 or less.
  • the second organic compound used in the organic light emitting device of the present invention is a delayed fluorescent material.
  • the third organic compound is also a delayed fluorescent material but differs from the second organic compound in the structure.
  • “Delayed fluorescent material” in the present invention is an organic compound which, in an excited state, undergoes reverse intersystem crossing from an excited triplet state to an excited singlet state, and which emits fluorescence (delayed fluorescence) in returning back from the excited singlet state to a ground state.
  • a compound which gives fluorescence having an emission lifetime of 100 ns (nanoseconds) or longer, when the emission lifetime is measured with a fluorescence lifetime measuring system e.g., streak camera system by Hamamatsu Photonics KK
  • a fluorescence lifetime measuring system e.g., streak camera system by Hamamatsu Photonics KK
  • the second organic compound is preferably such that the difference ⁇ E st between the lowest excited singlet energy level and the lowest excited triplet energy level at 77K is 0.3 eV or less, more preferably 0.25 eV or less, even more preferably 0.2 eV or less, further more preferably 0.15 eV or less, further more preferably 0.1 eV or less, further more preferably 0.07 eV or less, further more preferably 0.05 eV or less, further more preferably 0.03 eV or less, further more preferably 0.01 eV or less.
  • the third organic compound is preferably such that the difference ⁇ E st between the lowest excited singlet energy level and the lowest excited triplet energy level at 77K is 0.3 eV or less, more preferably 0.25 eV or less, even more preferably 0.2 eV or less, further more preferably 0.15 eV or less, further more preferably 0.1 eV or less, further more preferably 0.07 eV or less, further more preferably 0.05 eV or less, further more preferably 0.03 eV or less, further more preferably 0.01 eV or less.
  • a thermal activation type delayed fluorescent material can absorb heat generated by a device to relatively readily undergo reverse intersystem crossing from an excited triplet state to an excited singlet state, and can make the excited triplet energy efficiently contribute toward light emission.
  • the difference ⁇ E st between a lowest excited singlet energy level (E S1 ) and a lowest excited triplet energy level (E T1 ) of a compound is determined according to the following process.
  • AEs r is a value determined by calculating E S1 ⁇ E T1 .
  • a thin film or a toluene solution (concentration: 10 ⁇ 5 mol/L) of the targeted compound is prepared as a measurement sample.
  • the fluorescent spectrum of the sample is measured at room temperature (300 K).
  • the emission intensity is on the vertical axis and the wavelength is on the horizontal axis.
  • a tangent line is drawn to the rising of the emission spectrum on the short wavelength side, and the wavelength value ⁇ edge [nm] at the intersection between the tangent line and the horizontal axis is read.
  • the wavelength value is converted into an energy value according to the following conversion expression to calculate E S1 .
  • an LED light source by Thorlabs Corporation, M340L4
  • a detector by Hamamatsu Photonics K.K., PMA-12 Multichannel Spectroscope C10027-01).
  • the same sample as that for measurement of the lowest excited singlet energy (E S1 ) is cooled to 77 [K] with liquid nitrogen, and the sample for phosphorescence measurement is irradiated with excitation light (300 nm), and using a detector, the phosphorescence thereof is measured.
  • the emission after 100 milliseconds from irradiation with the excitation light is drawn as a phosphorescent spectrum.
  • a tangent line is drawn to the rising of the phosphorescent spectrum on the short wavelength side, and the wavelength value ⁇ edge [nm] at the intersection between the tangent line and the horizontal axis is read.
  • the wavelength value is converted into an energy value according to the following conversion expression to calculate E T1 .
  • the tangent line to the rising of the phosphorescent spectrum on the short wavelength side is drawn as follows. While moving on the spectral curve from the short wavelength side of the phosphorescent spectrum toward the maximum value on the shortest wavelength side among the maximum values of the spectrum, a tangent line at each point on the curve toward the long wavelength side is taken into consideration. With rising thereof (that is, with increase in the vertical axis), the inclination of the tangent line increases.
  • the tangent line drawn at the point at which the inclination value has a maximum value is referred to as the tangent line to the rising on the short wavelength side of the phosphorescent spectrum.
  • the maximum point having a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the above-mentioned shortest wavelength side, and the tangent line drawn at the point which is closest to the maximum value on the shortest wavelength side and at which the inclination value has a maximum value is referred to as the tangent line to the rising on the short wavelength side of the phosphorescent spectrum.
  • the first organic compound is an organic compound having a larger lowest excited singlet energy than the second organic compound, the third organic compound and the fourth organic compound, and has a function as a host material acting for transporting carriers or has a function of confining the energy of the fourth organic compound thereto. Accordingly, the fourth organic compound can efficiently change the energy having formed by recombination of holes and electrons in the molecule and the energy having received from the first organic compound, the second organic compound and the third organic compound, for light emission.
  • the first organic compound is preferably an organic compound having a hole transporting capability and an electron transporting capability, capable of preventing light emission from being in a longer wavelength range and having a high glass transition temperature.
  • the first organic compound is selected from compounds not emitting delayed fluorescence.
  • the second organic compound is a delayed fluorescent material having a smaller lowest excited singlet energy than the first organic compound and having a larger lowest excited singlet energy than the third organic compound and the fourth organic compound. Also the second organic compound is a delayed fluorescent material having a smaller lowest excited triplet energy than the first organic compound and having a larger lowest excited triplet energy than the third organic compound.
  • the second organic compound can be a compound capable of emitting delayed fluorescent under some conditions, and for the organic light emitting device of the present invention, it is not essential to emit delayed fluorescence derived from the second organic compound. In the organic light emitting device of the present invention, the second organic compound receives energy from the first organic compound in an excited singlet state to transition into an excited singlet state.
  • the second organic compound can receive energy from the first organic compound in an excited triplet state to transition into an excited triplet state.
  • the second organic compound has a small ⁇ E ST , and therefore the second organic compound in an excited triplet state can readily undergo reverse intersystem crossing to be a second organic compound in an excited singlet state.
  • the second organic compound in an excited singlet state that has been formed in such routes can give energy to the third organic compound and the fourth organic compound to make these compounds transition into an excited singlet state.
  • t-Bu represents a tertiary butyl group.
  • the third organic compound is a delayed fluorescent material having a smaller lowest excited singlet energy than the first organic compound, the second organic compound and the fourth organic compound, and is a delayed fluorescent material having a smaller lowest excited triplet energy than the first organic compound and the second organic compound.
  • the third organic compound can be a compound capable of emitting delayed fluorescent under some conditions, and for the organic light emitting device of the present invention, it is not essential to emit delayed fluorescence derived from the third organic compound.
  • the third organic compound plays a role of energy transfer from a part of the exciton formed in the second organic compound to the third organic compound to reduce the exciton load of the second organic compound.
  • the concentration of the third organic compound in the light emitting layer in the organic light emitting device of the present invention is smaller than the concentration of the first organic compound and the concentration of the second organic compound, and is 20% by weight or less.
  • the lowest excited triplet energy of the third organic compound is preferably smaller than the lowest excited triplet energy of the fourth organic compound.
  • the third organic compound can receive energy from the fourth organic compound in an excited triplet state to transition into an excited triplet state.
  • the third organic compound has a small ⁇ E ST , and therefore the third organic compound in an excited triplet state can readily undergo reverse intersystem crossing to be a third organic compound in an excited singlet state.
  • the third organic compound in an excited singlet state that has been formed in such routes can give energy to the fourth organic compound to make the fourth organic compound transition into an excited singlet state.
  • any other known delayed fluorescent materials than the above can be appropriately combined and used as the second organic compound and the third organic compound.
  • unknown delayed fluorescent materials can also be used.
  • WO2013/154064 paragraphs 0008 to 0048 and 0095 to 0133: WO2013/011954, paragraphs 0007 to 0047 and 0073-0085; WO2013/011955, paragraphs 0007 to 0033 and 0059 to 0066; WO2013/081088, paragraphs 0008 to 0071 and 0118 to 0133; JP 2013-256490 A, paragraphs 0009 to 0046 and 0093 to 0134; JP 2013-116975 A, paragraphs 0008 to 0020 and 0038 to 0040, WO2013/133359, paragraphs 0007 to 0032 and 0079 to 0084: WO2013/161437, paragraphs 0008 to 0054 and 0101-0121; JP 2014-9352 A, paragraphs 0007 to 0041 and 0060 to 0069; and JP 2014-9224 A, paragraphs 0008 to 0048 and 0067 to 0076;
  • a compound represented by the following general formula (1) and capable of emitting delayed fluorescence is preferably employed as the delayed fluorescent material in the present invention.
  • the compound represented by the general formula (1) can be employed as both the second organic compound and the third organic compound.
  • X 1 to X 5 each represent N or C—R.
  • R represents a hydrogen atom or a substituent.
  • these (C—R)'s can be the same as or different from each other.
  • at least one of X 1 to X 5 is C-D (where D represents a donor group).
  • Z represents an acceptor group
  • at least one of X 1 to X 5 is N, Z represents a hydrogen atom or a substituent.
  • X 1 to X 5 each represent N or C—R.
  • R represents a hydrogen atom or a substituent.
  • these (C—R)'s can be the same as or different from each other.
  • at least one of X 1 to X 5 is C-D (where D represents a donor group).
  • the acceptor group that Z in the general formula (1) represents is a group that donates an electron to the ring to which Z bonds, and for example, can be selected from groups having a positive Hammett's ⁇ p value.
  • the donor group that D in the general formula (1) and the general formula (2) represents is a group that attracts an electron from the ring to which D bonds, and for example, can be selected from groups having a negative Hammett's ⁇ p value.
  • the acceptor group can be referred to as A.
  • “Hammett's ⁇ p value” is one propounded by L. P. Hammett, and is one to quantify the influence of a substituent on the reaction rate or the equilibrium of a para-substituted benzene derivative. Specifically, the value is a constant ( ⁇ p ) peculiar to the substituent in the following equation that is established between a substituent and a reaction rate constant or an equilibrium constant in a para-substituted benzene derivative:
  • k represents a rate constant of a benzene derivative not having a substituent
  • k 0 represents a rate constant of a benzene derivative substituted with a substituent
  • K represents an equilibrium constant of a benzene derivative not having a substituent
  • K 0 represents an equilibrium constant of a benzene derivative substituted with a substituent
  • ⁇ represents a reaction constant to be determined by the kind and the condition of reaction.
  • X 1 to X 5 each represent N or C—R and at least one of them is C-D.
  • the number of N's of X 1 to X 5 is 0 to 4, and for example, a case where X 1 and X 3 and X 5 , X 1 and X 3 , X 1 and X 4 , X 5 and X 3 , X 1 and X 5 , X 2 and X 4 , X 1 alone, X 2 alone, or X 3 alone are/is N('s) can be exemplified.
  • the number of (C-D)'s of X 1 to X 5 is 1 to 5, and is preferably 2 to 5.
  • X 1 and X 2 and X 3 and X 4 and X 5 X 1 and X 2 and X 4 and X 5 .
  • X 1 and X 2 and X 3 and X 4 , X 1 and X 3 and X 4 and X 5 , X 1 and X 3 and X 5 , X 1 and X 2 and X 5 , X 1 and X 2 and X 4 , X 1 and X 3 and X 4 , X 1 and X 3 and X 4 , X 1 and X 3 , X 1 and X 4 , X 2 and X 1 , X 1 and X 5 , X 2 and X 4 , X 1 alone, X 2 alone, or X 3 alone are/is (C-DX's) can be exemplified.
  • At least one of X 1 to X 5 can be C-A.
  • A represents an acceptor group.
  • the number of (C-A)'s of X 1 to X 5 is preferably 0 to 2, more preferably 0 or 1.
  • a of C-A is preferably a cyano group.
  • X 1 to X 5 each can be independently C-D or C-A.
  • the two R's can bond to each other to form a cyclic structure.
  • the cyclic structure to be formed by bonding can be an aromatic ring or an aliphatic ring, or can contain a hetero atom, and further, the cyclic structure can also be a condensed ring of two or more rings.
  • the hetero atom is preferably selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • Examples of the cyclic structure to be formed include a benzene ring, a naphthalene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, an imidazoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentaene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cyclopentaene ring, a furan ring, a thiophene ring, a naphthyridine ring, a quinoxaline ring, and
  • the donor group D in the general formula (1) and the general formula (2) is preferably a group represented by, for example, the following general formula (3).
  • R 11 and R 12 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.
  • R 11 and R 12 can bond to each other to form a cyclic structure.
  • L represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • the substituent that can be introduced into the arylene group or the heteroarylene group of L can be the group represented by the general formula (1) or the general formula (2), or cab be a group represented by the general formulae (3) to (6) to be mentioned hereinunder.
  • the groups represented by these (1) to (6) can be introduced in an amount up to the maximum number of the groups capable of being introduced into L. In the case where plural groups of the general formulae (1) to (6) are introduced, these substituents can be the same as or different from each other.
  • * indicates the bonding position to the carbon atom (C) that constitutes the ring skeleton of the ring in the general formula (1) or the general formula (2).
  • alkyl group can be linear, branched or cyclic. Two or more of a linear moiety, a cyclic moiety and a branched moiety can be in the group as mixed.
  • the carbon number of the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. The carbon number can also be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • the alkyl group of a substituent can be further substituted with an aryl group.
  • Alkenyl group can be linear, branched or cyclic. Two or more of a linear moiety, a cyclic moiety and a branched moiety can be in the group as mixed.
  • the carbon number of the alkyl group can be, for example, 2 or more, or 4 or more. The carbon number can also be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkenyl group examples include an ethenyl group, an n-propenyl group, an isopropenyl group, an n-butenyl group, an isobutenyl group, an n-pentenyl group, an isopentenyl group, an n-hexenyl group, an isohexenyl group, and a 2-ethylhexenyl group.
  • the alkenyl group to be a substituent can be further substituted with an aryl group.
  • Aryl group and “Heteroaryl group” each can be a single ring or can be a condensed ring of two or more kinds of rings.
  • the number of the rings that are condensed is preferably 2 to 6, and, for example, can be selected from 2 to 4.
  • the ring include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a quinoline ring, a pyrazine ring, a quinoxaline ring, and a naphthyridine ring.
  • arylene ring or the heteroarylene ring include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group.
  • the substituent means a monovalent group that can substitute for a hydrogen atom, and does not mean a concept of condensation.
  • the group represented by the general formula (3) is preferably a group represented by any of the following general formulae (4) to (6).
  • R 51 to R 60 , R 61 to R 68 , and R 71 to R 78 each independently represent a hydrogen atom or a substituent.
  • R 51 to R 60 , R 61 to R 68 , and R 71 to R 78 each are also preferably a group represented by any of the above-mentioned general formulae (4) to (6).
  • the number of the substituents in the general formulae (4) to (6) is not specifically limited.
  • the description and the preferred examples of the cyclic structure reference can be made to the description and the preferred examples of the cyclic structure for X 1 to X 5 in the above-mentioned general formula (1) and general formula (2).
  • X represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom, a substituted or unsubstituted carbon atom, a substituted or unsubstituted silicon atom or a carbonyl group that is divalent and has a linking chain length of one atom, or represents a substituted or unsubstituted ethylene group, a substituted or unsubstituted vinylene group, a substituted or unsubstituted o-arylene group or a substituted or unsubstituted heteroarylene group that is divalent and has a linking chain length of two atoms.
  • substituents reference can be made to the description of the substituents in the general formula (1) and the general formula (2).
  • L 12 to L 14 each represent a single bond, a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • L 12 to L 14 each are preferably a single bond, or a substituted or unsubstituted arylene group.
  • the substituent for the arylene group and the heteroarylene group can be the group represented by the general formulae (1) to (6).
  • the group represented by the general formulae (1) to (6) can be introduced into L 12 to L 14 in an amount up to the maximum number of the substituents that can be introduced thereinto. In the case where plural groups of the general formulae (1) to (6) are introduced, these substituents can be the same as or different from each other.
  • * indicates the bonding position to the carbon atom (C) that constitutes the ring skeleton of the ring in the general formula (1) or the general formula (2).
  • a compound represented by the following general formula (7) and capable of emitting delayed fluorescence can be especially favorably used as the delayed fluorescent material in the present invention.
  • the compound represented by the general formula (7) can be employed both as the second organic compound and the third organic compound.
  • both the second organic compound and the third organic compound are compounds containing a dicyanobenzene structure.
  • R 1 to R 5 each represent a cyano group, at least one of R 1 to R 5 represents a substituted amino group, and the remaining R 1 to R 5 are hydrogen atoms, or represent any other substituent than a cyano group and a substituted amino group.
  • the substituted amino group is preferably a substituted or unsubstituted diarylamino group, and the two aryl groups constituting the substituted or unsubstituted diarylamino group can bond to each other.
  • the bonding can be made via a single bond (in such a case, a carbazole ring is formed), or via a linking group such as —O—, —S—, —N(R 6 )—, —C(R 7 )(R 8 )—, or —Si(R 9 )(R 10 )—.
  • R 6 to R 10 each represent a hydrogen atom or a substituent
  • R 7 and R 8 , and R 9 and R 10 each can bond to each other to form a cyclic structure.
  • a substituted amino group can be any of R 1 to R 5 , and for example, R 1 and R 2 , R 1 and R 3 , R 1 and R 4 , R 1 and R 5 , R 2 and R 3 , R 2 and R 4 , R 1 and R 2 and R 3 , R 1 and R 2 and R 4 , R 1 and R 2 and R , R 1 and R 3 and R 5 , R 1 and R 3 and R 5 , R 2 and R 3 and R 5 , R 1 and R 2 and R 1 and R 4 , R 1 and R 2 and R 3 and R 5 , R 1 and R 2 and R 4 and R 1 and R 2 and R 3 and R 5 , R 1 and R 2 and R 4 and R 5 , and R 1 and R 2 and R 1 and R 4 and R 5 each can be a substituted amino group.
  • a cyano group can also be any of R 1 to R 3 , and for example, R 1 , R 2 , R 3 , R 1 and R 2 , R 1 and R 3 , R 1 and R 4 , R 1 and R 5 , R 2 and R 3 , R 2 and R 4 , R 1 and R 2 and R 3 , R 1 and R 2 and R 4 , R 1 and R 2 and R 5 , R 1 and R 3 and R 4 , R 1 and R 3 and R 5 , and R 2 and R 3 and R 4 each can be a cyano group.
  • R 1 to R 5 that are neither a cyano group nor a substituted amino group each represent a hydrogen atom or a substituent.
  • substituent group A that contains a hydroxy group, a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton constituting atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton constituting atoms), a heteroaryloxy
  • a compound represented by the following general formula (8) and capable of emitting delayed fluorescence can also be especially preferably used as the delayed fluorescent material in the present invention.
  • the compound represented by the general formula (8) can be employed as both the second organic compound and the third organic compound.
  • any two of Y 1 , Y 2 and Y 3 are nitrogen atoms and the remaining one is a methine group, or all of Y 1 , Y 2 and Y 3 are nitrogen atoms.
  • Z 1 and Z 2 each independently represent a hydrogen atom or a substituent.
  • R 11 to R 18 each independently represent a hydrogen atom or a substituent, and at least one of R 11 to R 18 is preferably a substituted or unsubstituted arylamino group or a substituted or unsubstituted carbazolyl group.
  • the benzene ring to constitute the arylamino group and the benzene ring to constitute the carbazolyl group each can form a single bond or a linking group together with any of R 11 to R 18 .
  • the compound represented by the general formula (8) contains at least two carbazole structures in the molecule.
  • Examples of the substituent that Z 1 and Z 2 can take include the substituents in the above-mentioned substituent group A.
  • Specific examples of the substituent that R 11 to R 18 , the arylamino group and the carbazolyl group can take include the substituents in the substituent group A. and a cyano group, a substituted arylamino group and a substituted alkylamino group.
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , and R 17 and R 18 each can bond to each other to form a cyclic structure.
  • any two of Y 1 , Y 2 and Y 3 are nitrogen atoms and the remaining one is a methine group, or all of Y 1 , Y 2 and Y 3 are nitrogen atoms.
  • Z 2 represents a hydrogen atom or a substituent.
  • R 11 to R 18 and R 21 to R 28 each independently represent a hydrogen atom or a substituent. At least one of R 11 to R 18 and/or at least one of R 21 to R 28 are/is preferably a substituted or unsubstituted arylamino group or a substituted or unsubstituted carbazolyl group.
  • the benzene ring to constitute the arylamino group and the benzene ring to constitute the carbazolyl group each can form a single bond or a linking group together with any of R 11 to R 18 or R 21 to R 28 .
  • substituents that Z 2 can take include the substituents in the above-mentioned substituent group A.
  • R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , and R 27 and R 28 each can bond to each other to form a cyclic structure.
  • a compound represented by the following general formula (10) and capable of emitting delayed fluorescence can be especially preferably used as the delayed fluorescent material in the present invention.
  • the compound represented by the general formula (10) can be employed as the third organic compound.
  • A represents a cyano group, or a substituted or unsubstituted triazinyl group.
  • R A to R E is/are an alkyl group, three or four of R A to R E each are a donor group, and the remaining R A to R E each are a hydrogen atom or a deuterium atom.
  • the triazinyl group preferably contains a 1,3,5-triazine ring.
  • substituent for the triazinyl group reference can be made to the description of the substituent in the general formula (7), and the substituent is preferably an aryl group.
  • the donor group reference can be made to the description and the preferred range of the donor group that D represents in the general formula (1) and the general formula (2).
  • a part or all of the donor groups existing in the general formula (10) are preferably a substituted or unsubstituted carbazolyl group represented by the above-mentioned general formula (5).
  • the general formula (10) has donor groups differing in the structure.
  • the general formula (10) has carbazolyl groups differing in the substituent condition, and can have, for example, both a substituted carbazolyl group and an unsubstituted carbazolyl group.
  • R A and R B are donor groups having the same structure
  • R D and R E can be donor groups differing from R A and R B in the structure.
  • all the donor groups in the general formula (10) can have the same structure.
  • the number of alkyl groups preferably, one of R A to R E is an alkyl group. In a preferred embodiment of the present invention, one of R A to R E is an alkyl group, and four of R A to R E are donor groups.
  • one of R A to R E is an alkyl group, three of R A to R E are donor groups, and the remaining one is a hydrogen atom.
  • R C is an alkyl group. A part or all of the hydrogen atoms existing in the compound represented by the general formula (10) can be substituted with a deuterium atom.
  • a compound represented by the following general formula (11) and capable of emitting delayed fluorescence can be especially preferably used as the delayed fluorescent material in the present invention.
  • the compound represented by the general formula (11) can be employed as the third organic compound.
  • A represents a cyano group, or a substituted or unsubstituted triazinyl group.
  • Three to five of R a to R e each represent a donor group, and the remaining R a to R e each represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
  • At least one donor group represented by R a to R e is a condensed ring carbazolyl group.
  • the condensed ring carbazolyl group means a carbazol-9-yl group in which at least one of the two benzene rings constituting the carbazole ring is condensed with a ring structure.
  • Both the two benzene rings can be condensed with a ring structure.
  • both the condensed skeleton structures are the same, more preferably the two are the same structure.
  • the position not condensed with a ring can be substituted, and in the case where the position is substituted, preferably, the 3-position or the 6-position of the carbazole ring is substituted.
  • the substituent is a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted phenyl group, and for example, a phenyl group or a deuterium atom-substituted phenyl group can be preferably employed.
  • a part or all of the hydrogen atoms existing in the compound represented by the general formula (11) can be substituted with a deuterium atom.
  • the condensed ring carbazolyl group includes a benzofuran-condensed carbazol-9-yl group in which the carbazol ring is condensed with a benzofuran ring at the 2,3-positions, a benzothiophene-condensed carbazol-9-yl group in which the carbazol ring is condensed with a benzothiophene ring at the 2,3-positions, an indole-condensed carbazol-9-yl group in which the carbazol ring is condensed with an indole ring at the 2,3-positions, an indene-condensed carbazol-9-yl group in which the carbazol ring is condensed with an indene ring at the 2,3-positions, and a silaindene-condensed carbazol-9-yl group in which the carbazol ring is condensed with a silaindene ring at the 2.3-positions.
  • the hetero atom to constitute the condensed ring bonds at the 2-position in the case where the rings are condensed at the 2,3-positions of the carbazole ring, preferably the hetero atom to constitute the condensed ring bonds at the 3-position, and in the case where the rings are condensed at the 3,4-positions of the carbazole ring, preferably the hetero atom to constitute the condensed ring bonds at the 4-position.
  • the fourth organic compound is a delayed fluorescent material having a smaller lowest excited singlet energy than the first organic compound and the second organic compound and having a larger lowest excited singlet energy than the third organic compound.
  • the organic light emitting device of the present invention emits fluorescence derived from the fourth organic compound.
  • Light emission from the fourth organic compound generally includes delayed fluorescence.
  • the maximum component of light emission from the organic light emitting device of the present invention is light emission from the fourth organic compound. Namely, among the light emission from the organic light emitting device of the present invention, the amount of light emission from the fourth organic compound is the largest.
  • the fourth organic compound receives energy from the first organic compound and the second organic compound in an excited singlet state and from the second organic compound having been in an excited singlet state through reverse intersystem crossing from an excited triplet state, and thus transitions into an excited singlet state. Also in a preferred embodiment of the present invention, the fourth organic compound receives energy from the third organic compound in an excited singlet state and from the third organic compound having been in an excited singlet state through reverse intersystem crossing from an excited triplet state, and thus transitions into an excited singlet state. The resultant fourth organic compound thus m an excited singlet state emits fluorescence when thereafter returning back to the ground state.
  • the fluorescent material to be used as the fourth organic compound can be any one with no specific limitation so far as it can receive energy from the first organic compound, the second organic compound and the third organic compound to emit light, and the light emission can include any of fluorescence, delayed fluorescence, and phosphorescence.
  • the light emission includes fluorescence and delayed fluorescence, and more preferably the maximum component of light emission from the fourth organic compound is delayed fluorescence.
  • the fourth organic compound two or more kinds can be used so far as they satisfy the requirements in the present invention.
  • two or more kinds of the fourth organic compounds differing in the emission color light of a desired color can be emitted.
  • monochromatic emission can be made by the fourth organic compound.
  • the maximum emission wavelength of the compound usable as the fourth organic compound is not specifically limited. Therefore, a light emitting material having a maximum emission wavelength in a visible range (380 to 780 nm) or having a maximum emission wavelength in an IR range (780 nm to 1 mm) can be appropriately selected and used here. Preferred is a fluorescent material having a maximum emission wavelength in a visible range.
  • a light emitting material of which the maximum emission wavelength in a range of 380 to 780 nm falls within a range of 380 to 570 nm can be selected and used, or a light emitting material of which the maximum emission wavelength falls within a range of 380 to 500 nm can be selected and used, or a light emitting material of which the maximum emission wavelength falls within a range of 380 to 480 nm can be selected and used, or a light emitting material of which the maximum emission wavelength falls within a range of 420 to 480 nm can be selected and used.
  • the second organic compound and the fourth organic compound are so selected and combined that the emission wavelength range of the former and the emission wavelength range of the latter can overlap with each other.
  • the edge in the long wavelength side of the emission spectrum of the second organic compound overlaps with the edge on the short wavelength side of the absorption spectrum of the fourth organic compound.
  • the third organic compound and the fourth organic compound are so selected and combined that there can be overlapping between the emission wavelength range of the former and the absorption wavelength range of the latter.
  • Et represents an ethyl group.
  • a preferred compound group includes Compounds E1 to E1 and derivatives having a skeleton thereof.
  • the derivatives include compounds substituted with an alkyl group, an aryl group, a heteroaryl group or a diarylamino group.
  • the light emitting layer in the organic light emitting device of the present invention contains the first organic compound, the second organic compound, the third organic compound and the fourth organic compound satisfying the requirements (a) to (e).
  • the light emitting layer can be so configured that it does not contain a compound and a metal element that donate or accept charge and energy, except the first organic compound, the second organic compound, the third organic compound and the fourth organic compound.
  • the light emitting layer can be so configured as to be composed of only the first organic compound, the second organic compound, the third organic compound and the fourth organic compound.
  • the light emitting layer can be composed of compounds alone each formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, a boron atom, an oxygen atom and a sulfur atom.
  • the light emitting layer can be composed of compounds alone each formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, a boron atom and an oxygen atom.
  • the light emitting layer can be composed of compounds alone each formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, a boron atom and a sulfur atom.
  • the light emitting layer can be composed of compounds alone each formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom and a boron atom.
  • the light emitting layer can be composed of compounds alone each formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, oxygen atom and a sulfur atom.
  • the light emitting layer can be composed of compounds alone each formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom and a nitrogen atom.
  • the first organic compound, the second organic compound and the third organic compound contained in the light emitting layer can be each independently a compound formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, an oxygen atom and a sulfur atom.
  • the first organic compound, the second organic compound and the third organic compound can be each independently a compound formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom and an oxygen atom.
  • the first organic compound, the second organic compound and the third organic compound can be each independently a compound formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom and a sulfur atom.
  • the first organic compound, the second organic compound and the third organic compound can be each independently a compound formed of atoms selected from the group consisting of a carbon atom, a hydrogen atom and a nitrogen atom.
  • the light emitting layer can be formed by co-evaporation of the first organic compound, the second organic compound, the third organic compound and the fourth organic compound, or can be formed by coating method that uses a solution prepared by dissolving the first organic compound, the second organic compound, the third organic compound and the fourth organic compound.
  • the light emitting layer is formed by co-evaporation, two or more of the first organic compound, the second organic compound, the third organic compound and the fourth organic compound are previously mixed and put into a crucible or the like to be an evaporation source, and using the evaporation source, the light emitting layer can be formed by co-evaporation.
  • the second organic compound, the third organic compound and the fourth organic compound are previously mixed to form one evaporation source, and using the evaporation source and an evaporation source of the first organic compound, the light emitting layer can be formed by co-evaporation.
  • an excellent organic light emitting device such as an organic photoluminescent device (organic PL device) and an organic electroluminescent device (organic EL device).
  • the thickness of the light emitting layer can be 1 to 15 nm, or can be 2 to 10 nm or can be 3 to 7 nm.
  • the organic photoluminescent device is so configured as to have at least a light emitting layer formed on a substrate.
  • the organic electroluminescent device is so configured as to have at least an anode, a cathode and an organic layer formed between the anode and the cathode.
  • the organic layer contains at least a light emitting layer, and can be composed of a light emitting layer, or can have at least one other organic layer in addition to the light emitting layer.
  • Such other organic layers include hole transporting layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transporting layer and an exciton barrier layer.
  • the hole transporting layer can also be a hole injection and transporting layer having a hole injection function
  • the electron transporting layer can also be an electron injection transporting layer having an electron injection function.
  • FIG. 1 A specific configuration example of an organic electroluminescent device is shown in FIG. 1 .
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is a hole transporting layer
  • 5 is a light emitting layer
  • 6 is an electron transporting layer
  • 7 is a cathode.
  • the device can be so designed that shortest wavelength emission contains delayed fluorescence.
  • the device can be so designed that shortest wavelength emission does not contain delayed fluorescence.
  • the organic electroluminescent device of the invention is supported by a substrate, wherein the substrate is not particularly limited and may be any of those that have been commonly used in an organic electroluminescent device, for example those formed of glass, transparent plastics, quartz and silicon.
  • the anode of the organic electroluminescent device is made of a metal, an alloy, an electroconductive compound, or a combination thereof.
  • the metal, alloy, or electroconductive compound has a large work function (4 eV or more).
  • the metal is Au.
  • the electroconductive transparent material is selected from CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material capable of forming a transparent electroconductive film such as IDIXO (In 2 O 3 —ZnO), is be used.
  • the anode is a thin film. In some embodiments the thin film is made by vapor deposition or sputtering.
  • the film is patterned by a photolithography method.
  • the pattern may not require high accuracy (for example, approximately 100 ⁇ m or more)
  • the pattern may be formed with a mask having a desired shape on vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method and a coating method is used.
  • the anode when the emitted light goes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred Ohm per square or less.
  • the thickness of the anode is from 10 to 1,000 nm. In some embodiments, the thickness of the anode is from 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.
  • the cathode is made of an electrode material a metal having a small work function (4 eV or less) (referred to as an electron injection metal), an alloy, an electroconductive compound, or a combination thereof.
  • the electrode material is selected from sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-cupper mixture, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al 2 O 3 ) mixture, indium, a lithium-aluminum mixture, and a rare earth metal.
  • a mixture of an electron injection metal and a second metal that is a stable metal having a larger work function than the electron injection metal is used.
  • the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al 2 O 3 ) mixture, a lithium-aluminum mixture, and aluminum.
  • the mixture increases the electron injection property and the durability against oxidation.
  • the cathode is produced by forming the electrode material into a thin film by vapor deposition or sputtering.
  • the cathode has a sheet resistance of several hundred Ohm per square or less.
  • the thickness of the cathode ranges from 10 nm to 5 ⁇ m.
  • the thickness of the cathode ranges from 50 to 200 nm.
  • any one of the anode and the cathode of the organic electroluminescent device is transparent or translucent. In some embodiments, the transparent or translucent electroluminescent devices enhances the light emission luminance.
  • the cathode is formed with an electroconductive transparent material, as described for the anode, to form a transparent or translucent cathode.
  • a device comprises an anode and a cathode, both being transparent or translucent.
  • An injection layer is a layer between the electrode and the organic layer.
  • the injection layer decreases the driving voltage and enhances the light emission luminance.
  • the injection layer includes a hole injection layer and an electron injection layer.
  • the injection layer can be positioned between the anode and the light-emitting layer or the hole transporting layer, and between the cathode and the light-emitting layer or the electron transporting layer.
  • an injection layer is present. In some embodiments, no injection layer is present.
  • Preferred compound examples for use as a hole injection material are shown below.
  • a barrier layer is a layer capable of inhibiting charges (electrons or holes) and/or excitons present in the light-emitting layer from being diffused outside the light-emitting layer.
  • the electron barrier layer is between the light-emitting layer and the hole transporting layer, and inhibits electrons from passing through the light-emitting layer toward the hole transporting layer.
  • the hole barrier layer is between the light-emitting layer and the electron transporting layer, and inhibits holes from passing through the light-emitting layer toward the electron transporting layer.
  • the barrier layer inhibits excitons from being diffused outside the light-emitting layer.
  • the electron barrier layer and the hole barrier layer are exciton barrier layers.
  • the term “electron barrier layer” or “exciton barrier layer” includes a layer that has the functions of both electron barrier layer and of an exciton barrier layer.
  • a hole barrier layer acts as an electron transporting layer.
  • the hole barrier layer inhibits holes from reaching the electron transporting layer while transporting electrons.
  • the hole barrier layer enhances the recombination probability of electrons and holes in the light-emitting layer.
  • the material for the hole barrier layer may be the same materials as the ones described for the electron transporting layer.
  • Preferred compound examples for use for the hole barrier layer are shown below.
  • the electron barrier layer transports holes.
  • the electron barrier layer inhibits electrons from reaching the hole transporting layer while transporting holes.
  • the electron barrier layer enhances the recombination probability of electrons and holes in the light-emitting layer.
  • Preferred compound examples for use as the electron barrier material are shown below.
  • An exciton barrier layer inhibits excitons generated through recombination of holes and electrons in the light-emitting layer from being diffused to the charge transporting layer.
  • the exciton barrier layer enables effective confinement of excitons in the light-emitting layer.
  • the light emission efficiency of the device is enhanced.
  • the exciton barrier layer is adjacent to the light-emitting layer on any of the side of the anode and the side of the cathode, and on both the sides. In some embodiments, where the exciton barrier layer is on the side of the anode, the layer can be between the hole transporting layer and the light-emitting layer and adjacent to the light-emitting layer.
  • the layer can be between the light-emitting layer and the cathode and adjacent to the light-emitting layer.
  • a hole injection layer, an electron barrier layer, or a similar layer is between the anode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the anode.
  • a hole injection layer, an electron barrier layer, a hole barrier layer, or a similar layer is between the cathode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the cathode.
  • the exciton barrier layer comprises excited singlet energy and excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy of the light-emitting material, respectively.
  • the hole transporting layer comprises a hole transporting material.
  • the hole transporting layer is a single layer.
  • the hole transporting layer comprises a plurality layers.
  • the hole transporting material has one of injection or transporting property of holes and barrier property of electrons.
  • the hole transporting material is an organic material.
  • the hole transporting material is an inorganic material. Examples of known hole transporting materials that may be used herein include but are not limited to a triazole derivative, an oxadiazole derivative, an imidazole derivative, a carbazole derivative, an indolocarbazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, an oxazole derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aniline copolymer and an electroconductive polymer oligomer, particularly a thiophene
  • the hole transporting material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transporting material is an aromatic tertiary amine compound. Preferred compound examples for use as the hole transporting material are shown below.
  • the electron transporting layer comprises an electron transporting material.
  • the electron transporting layer is a single layer.
  • the electron transporting layer comprises a plurality of layer.
  • the electron transporting material needs only to have a function of transporting electrons, which are injected from the cathode, to the light-emitting layer.
  • the electron transporting material also function as a hole barrier material.
  • the electron transporting layer that may be used herein include but are not limited to a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyran dioxide derivative, carbodiimide, a fluorenylidene methane derivative, anthraquinodimethane, an anthrone derivatives, an azole derivative, an azine derivative, an oxadiazole derivative, or a combination thereof, or a polymer thereof.
  • the electron transporting material is a thiadiazole derivative, or a quinoxaline derivative.
  • the electron transporting material is a polymer material. Preferred compound examples for use as the electron transporting material are shown below.
  • an light emitting layer is incorporated into a device.
  • the device includes, but is not limited to an OLED bulb, an OLED lamp, a television screen, a computer monitor, a mobile phone, and a tablet.
  • an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising a light emitting layer between the anode and the cathode.
  • compositions described herein may be incorporated into various light-sensitive or light-activated devices, such as a OLEDs or photovoltaic devices.
  • the composition may be useful in facilitating charge transfer or energy transfer within a device and/or as a hole-transport material.
  • the device may be, for example, an organic light-emitting diode (OLED), an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin-film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a light-emitting electrochemical cell (LEC) or an organic laser diode (O-laser).
  • OLED organic light-emitting diode
  • O-IC organic integrated circuit
  • O-FET organic field-effect transistor
  • OFTFT organic thin-film transistor
  • O-LET organic light-emitting transistor
  • O-SC organic solar cell
  • O-SC organic optical detector
  • O-FQD organic field-quench device
  • LEC light-emitting electrochemical cell
  • O-laser organic laser diode
  • an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising a light emitting layer between the anode and the cathode.
  • a device comprises OLEDs that differ in color.
  • a device comprises an array comprising a combination of OLEDs.
  • the combination of OLEDs is a combination of three colors (e.g., RGB).
  • the combination of OLEDs is a combination of colors that are not red, green, or blue (for example, orange and yellow green).
  • the combination of OLEDs is a combination of two, four, or more colors.
  • a device is an OLED light comprising.
  • circuit board having a first side with a mounting surface and an opposing second side, and defining at least one aperture
  • At least one OLED on the mounting surface the at least one OLED configured to emanate light, comprising:
  • At least one connector arranged at an end of the housing, the housing and the connector defining a package adapted for installation in a light fixture.
  • the OLED light comprises a plurality of OLEDs mounted on a circuit board such that light emanates in a plurality of directions. In some embodiments, a portion of the light emanated in a first direction is deflected to emanate in a second direction. In some embodiments, a reflector is used to deflect the light emanated in a first direction.
  • the compounds of the invention can be used in a screen or a display.
  • the compounds of the invention are deposited onto a substrate using a process including, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in a two-sided etch provides a unique aspect ratio pixel.
  • the screen (which may also be referred to as a mask) is used in a process in the manufacturing of OLED displays.
  • the corresponding artwork pattern design facilitates a very steep and narrow tie-bar between the pixels in the vertical direction and a large, sweeping bevel opening in the horizontal direction. This allows the close patterning of pixels needed for high definition displays while optimizing the chemical deposition onto a TFT backplane.
  • the internal patterning of the pixel allows the construction of a 3-dimensional pixel opening with varying aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged “stripes” or halftone circles within the pixel area inhibits etching in specific areas until these specific patterns are undercut and fall off the substrate. At that point the entire pixel area is subjected to a similar etch rate but the depths are varying depending on the halftone pattern. Varying the size and spacing of the halftone pattern allows etching to be inhibited at different rates within the pixel allowing for a localized deeper etch needed to create steep vertical bevels.
  • a preferred material for the deposition mask is invar.
  • Invar is a metal alloy that is cold rolled into long thin sheet in a steel mill. Invar cannot be electrodeposited onto a rotating mandrel as the nickel mask.
  • a preferred and more cost feasible method for forming the open areas in the mask used for deposition is through a wet chemical etching.
  • a screen or display pattern is a pixel matrix on a substrate.
  • a screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).
  • a screen or display pattern is fabricated using a wet chemical etch.
  • a screen or display pattern is fabricated using plasma etching.
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel in units of cell panels.
  • each of the cell panels on the mother panel is formed by forming a thin film transistor (TFT) including an active layer and a source/drain electrode on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then is cut from the mother panel.
  • TFT thin film transistor
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel in units of cell panels.
  • each of the cell panels on the mother panel is formed by forming a thin film transistor (TFT) including an active layer and a source/drain electrode on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then is cut from the mother panel.
  • TFT thin film transistor
  • OLED organic light-emitting diode
  • the barrier layer is an inorganic film formed of, for example, SiNx, and an edge portion of the barrier layer is covered with an organic film formed of polyimide or acryl.
  • the organic film helps the mother panel to be softly cut in units of the cell panel.
  • the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and a source/drain electrode.
  • Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein the organic film applied to the interface portion is formed of a same material as a material of the planarization film and is formed at a same time as the planarization film is formed.
  • a light-emitting unit is connected to the TFT layer with a passivation layer and a planarization film therebetween and an encapsulation layer that covers and protects the light-emitting unit.
  • the organic film contacts neither the display units nor the encapsulation layer.
  • each of the organic film and the planarization film may include any one of polyimide and acryl.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide. The method may further include, before the forming of the barrier layer on one surface of the base substrate formed of polyimide, attaching a carrier substrate formed of a glass material to another surface of the base substrate, and before the cutting along the interface portion, separating the carrier substrate from the base substrate.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer.
  • the planarization film is an organic film formed on the passivation layer.
  • the planarization film is formed of polyimide or acryl, like the organic film formed on the edge portion of the barrier layer.
  • the planarization film and the organic film are simultaneously formed when the OLED display is manufactured.
  • the organic film may be formed on the edge portion of the barrier layer such that a portion of the organic film directly contacts the base substrate and a remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.
  • the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrode is connected to the source/drain electrode of the TFT layer.
  • an image forming unit including the TFT layer and the light-emitting unit is referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed to have a thin film encapsulation structure in which an organic film and an inorganic film are alternately stacked.
  • the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are stacked.
  • the organic film applied to the interface portion is spaced apart from each of the plurality of display units.
  • the organic film is formed such that a portion of the organic film directly contacts the base substrate and a remaining portion of the organic film contacts the barrier layer while surrounding an edge portion of the barrier layer.
  • the OLED display is flexible and uses the soft base substrate formed of polyimide.
  • the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.
  • the barrier layer is formed on a surface of the base substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to a size of each of the cell panels. For example, while the base substrate is formed over the entire surface of a mother panel, the barrier layer is formed according to a size of each of the cell panels, and thus a groove is formed at an interface portion between the barrier layers of the cell panels. Each of the cell panels can be cut along the groove.
  • the method of manufacture further comprises cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of the organic film is formed in the groove, and wherein the groove does not penetrate into the base substrate.
  • the TFT layer of each of the cell panels is formed, and the passivation layer which is an inorganic film and the planarization film which is an organic film are disposed on the TFT layer to cover the TFT layer.
  • the planarization film formed of, for example, polyimide or acryl is formed, the groove at the interface portion is covered with the organic film formed of, for example, polyimide or acryl.
  • each of the cell panels may be softly cut and cracks may be prevented from occurring in the barrier layer.
  • the organic film covering the groove at the interface portion and the planarization film are spaced apart from each other.
  • the organic film and the planarization film are connected to each other as one layer, since external moisture may penetrate into the display unit through the planarization film and a portion where the organic film remains, the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.
  • the display unit is formed by forming the light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit.
  • the carrier substrate that supports the base substrate is separated from the base substrate.
  • the carrier substrate is separated from the base substrate due to a difference in a thermal expansion coefficient between the carrier substrate and the base substrate.
  • the mother panel is cut in units of the cell panels. In some embodiments, the mother panel is cut along an interface portion between the cell panels by using a cutter. In some embodiments, since the groove at the interface portion along which the mother panel is cut is covered with the organic film, the organic film absorbs an impact during the cutting. In some embodiments, cracks may be prevented from occurring in the barrier layer during the cutting.
  • the methods reduce a defect rate of a product and stabilize its quality.
  • an OLED display including: a barrier layer that is formed on a base substrate: a display unit that is formed on the barrier layer; an encapsulation layer that is formed on the display unit; and an organic film that is applied to an edge portion of the barrier layer.
  • ITO indium tin oxide
  • thin films were laminated at a vacuum degree of 1 ⁇ 10 ⁇ 6 Pa according to a vacuum evaporation method.
  • HATCN was deposited on ITO at a thickness of 10 nm
  • NPD was deposited thereon at a thickness of 30 nm.
  • TrisPCz was formed at a thickness of 10 nm.
  • the compound H3 was formed at a thickness of 3 nm.
  • the compound H3, the compound T10, the compound S1 and the compound E1 were co-evaporated from different evaporation sources each at the concentration shown in the following Table to form a layer having a thickness of 30 nm to be alight emitting layer.
  • SF3TRZ was formed at a thickness of 10 nm as a hole barrier layer.
  • SF3TRZ and Liq were co-evaporated from different evaporation sources to form a layer having a thickness of 30 nm to be an electron transporting layer.
  • SF3TRZ/Liq (by weight) was 7.3.
  • Example 1 Example 1
  • Example 2 Example 3
  • the compound H3 of the first organic compound, the compound T10 of the second organic compound, the compound S1 of the third organic compound and the compound E1 of the fourth organic compound satisfied the requirements (a) to (e).
  • the thus-produced organic electroluminescent devices were energized to emit delayed fluorescence derived from the fourth organic compound, and each attained a high external quantum yield of 15% or more. Regarding the emission from the organic electroluminescent devices, it was confirmed that the emission amount derived from the fourth organic compound was the maximum and the color purity was high in every device (maximum emission wavelength 471 nm). Each organic electroluminescent device was analyzed to measure the driving voltage to realize 750 cm/m 2 and the time-dependent change of emission intensity, and the results are shown in FIG. 2 . The emission intensity and the driving voltage are shown as a relative value based on the initial value of 1.
  • Organic electroluminescent devices were produced using the compound S2 or the compound S3 as the third organic compound in place of the compound S1 used in Example 3. These devices both satisfied the requirements (a) to (e).
  • Example 4 and Example 5 gave light emission with high color purity derived from the fourth organic compound therein, and it is confirmed that the lifetime thereof is longer than in Comparative Example 1.
  • an organic light emitting device having along lifetime with high color purity. Accordingly, the industrial applicability of the present invention is great.

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EP4489552A4 (en) * 2022-03-04 2025-06-11 Kyulux, Inc. ORGANIC ELECTROLUMINESCENT ELEMENT, METHOD FOR EVALUATING DELAYED FLUORESCENCE MATERIAL, METHOD FOR DESIGNING DELAYED FLUORESCENCE MATERIAL, METHOD FOR DESIGNING ORGANIC ELECTROLUMINESCENT ELEMENT, AND PROGRAM
EP4489554A4 (en) * 2022-03-04 2025-06-11 Kyulux, Inc. ORGANIC ELECTROLUMINESCENT ELEMENT, METHOD FOR EVALUATING DELAYED FLUORESCENCE MATERIAL, METHOD FOR DESIGNING DELAYED FLUORESCENCE MATERIAL, METHOD FOR DESIGNING ORGANIC ELECTROLUMINESCENT ELEMENT, AND PROGRAM
EP4489553A4 (en) * 2022-03-04 2025-07-23 Kyulux Inc ORGANIC ELECTROLUMINESCENT ELEMENT, METHOD FOR EVALUATING DELAYED FLUORESCENCE MATERIAL, METHOD FOR DESIGNING DELAYED FLUORESCENCE MATERIAL, METHOD FOR DESIGNING ORGANIC ELECTROLUMINESCENT ELEMENT, AND PROGRAM

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US20240298538A1 (en) 2024-09-05
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