WO2010143434A1 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2010143434A1 WO2010143434A1 PCT/JP2010/003869 JP2010003869W WO2010143434A1 WO 2010143434 A1 WO2010143434 A1 WO 2010143434A1 JP 2010003869 W JP2010003869 W JP 2010003869W WO 2010143434 A1 WO2010143434 A1 WO 2010143434A1
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- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H10K59/35—Devices specially adapted for multicolour light emission comprising red-green-blue [RGB] subpixels
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Definitions
- the present invention relates to an organic electroluminescence (EL) element, particularly a highly efficient organic EL element.
- EL organic electroluminescence
- organic EL elements When organic EL elements are classified according to their light emission principles, they can be divided into two types: fluorescent and phosphorescent types.
- fluorescent and phosphorescent types When a voltage is applied to the organic EL element, holes are injected from the anode and electrons are injected from the cathode, and these recombine in the light emitting layer to form excitons.
- the formed excitons become singlet excitons and triplet excitons according to the statistical rule of electron spin, which are generated at a ratio of 25%: 75%. For this reason, it is said that the internal quantum efficiency of fluorescence emission by singlet excitons is limited to 25%.
- a fluorescent element using a fluorescent material has recently been developed with a long-life technology and is being applied to a full-color display such as a mobile phone or a television. However, high efficiency has been a problem.
- Non-Patent Document 1 a non-doped element using an anthracene compound as a host material is analyzed, and as a mechanism, singlet excitons are generated by collisional fusion of two triplet excitons. Fluorescence emission is increasing.
- Non-Patent Document 1 only discloses that an increase in fluorescence emission is confirmed by collisional fusion of triplet excitons in a non-doped element composed of only a host material. The increase was as low as 3-6%.
- Non-Patent Document 2 reports that the blue quantum element has an internal quantum efficiency of 28.5%, which exceeds the conventional theoretical limit of 25%. However, no technical means for exceeding 25% has been disclosed, and further higher efficiency has been demanded from the viewpoint of practical use of a full-color organic EL television.
- Patent Document 1 Another example using triplet excitons in a fluorescent element is disclosed in Patent Document 1.
- the lowest triplet excited state (T1) is lower than the lowest singlet excited state (S1), but the higher triplet excited state (T2) may be higher than S1.
- the external quantum efficiency is about 6% (when the light extraction efficiency is 25%, the internal quantum efficiency is 24%), which does not exceed the limit value of 25% that has been conventionally known.
- the mechanism here is due to intersystem crossing from a triplet excited state to a singlet excited state in one molecule, and the two triplet excitons disclosed in Non-Patent Document 1 The singlet generation phenomenon due to the collision has not occurred.
- phenanthroline derivatives such as BCP (Bathocuproin) and BPhen are used for the hole blocking layer in the fluorescent element, thereby increasing the density of holes at the interface between the hole blocking layer and the light emitting layer, and efficiently. Techniques for causing recombination are disclosed.
- phenanthroline derivatives such as BCP (basocuproin) and BPhen are vulnerable to holes, have poor oxidation durability, and have insufficient performance from the viewpoint of extending the lifetime of the device.
- Patent Documents 4 and 5 disclose examples in which an aromatic compound such as an anthracene derivative is used as a material for an electron transport layer in contact with a light emitting layer in a fluorescent element.
- an aromatic compound such as an anthracene derivative
- the triplet energy of the electron transport layer normally designed in so-called phosphorescent devices.
- the triplet energy of the electron transport layer is smaller than the triplet energy of the light-emitting layer, so that triplet excitons generated in the light-emitting layer are actually transported by electrons. It has been diffused to the layer and then undergoes a thermal deactivation process, and it has been difficult to exceed 25%, which is the theoretical limit value of conventional fluorescence.
- Patent Document 6 discloses a device using a fluoranthene dopant exhibiting long-life and high-efficiency blue light emission, but it is not necessarily high-efficiency.
- the phosphorescent type uses light emitted directly from triplet excitons. Since singlet excitons are also converted into triplet excitons by spin conversion inside the light emitting molecule, in principle, it is expected that an internal luminous efficiency of nearly 100% can be obtained. Therefore, since a phosphorescent light emitting device using an Ir complex was announced by Forrest et al. In 2000, a phosphorescent light emitting device has attracted attention as a technique for improving the efficiency of organic EL devices. However, although red phosphorescent devices have reached the practical application range, green and blue phosphorescent devices have a shorter lifetime than fluorescent-type devices, and in particular, blue phosphorescence has insufficient color purity and luminous efficiency. The current situation is that it has not been put into practical use.
- the light emitting layer is separately coated with a blue fluorescent light emitting layer, a green phosphorescent light emitting layer, and a red phosphorescent light emitting layer.
- the manufacturing process is reduced and mass production is facilitated.
- the blue fluorescent light-emitting layer, the green phosphorescent light-emitting layer, and the red phosphorescent light-emitting layer have greatly different physical property values such as affinity, ionization potential, and energy gap. Therefore, when the peripheral layer is a common layer, the green phosphorescent light emitting layer with the largest energy gap is designed to optimize the carrier injection property, and the performance of other light emitting layers (especially the blue fluorescent light emitting layer) The decline was happening.
- a light emitting layer is composed of a blue light emitting layer containing a fluorescent light emitting dopant, a green light emitting layer containing a phosphorescent light emitting dopant, and a red light emitting layer containing a phosphorescent light emitting dopant, and the hole suppressing layer is a common layer.
- the element provided as is described.
- the manufacturing process is reduced by using the hole suppression layer as a common layer, electron injection from the hole barrier layer to each light emitting layer has become a problem by using the hole suppression layer as a common layer.
- the difference in affinity between the blue light-emitting layer and the hole-inhibiting layer is as small as about 0.2 eV.
- the green light-emitting layer uses a material with low affinity such as CBP, the affinity with the hole-inhibiting layer. The difference is large, about 0.6 eV. For this reason, the electron injection property is lowered in the green light emitting layer, and the drive voltage is increased. Furthermore, since the coupling region is concentrated at the interface between the green phosphorescent light emitting layer and the hole suppressing layer, exciton diffusion is large and the light emitting efficiency of the green light emitting layer does not increase.
- Patent Document 10 discloses an organic EL element in which an affinity difference ⁇ Af between a light-emitting layer containing a phosphorescent dopant and an electron transport layer is 0.2 ⁇ Af ⁇ 0.65 eV. However, when the blue light emitting layer, the green light emitting layer, and the red light emitting layer are separately applied, no disclosure is made regarding the efficiency of the light emitting layer.
- Triplet-Triplet Fusion TTF phenomenon
- the triplet excitons are confined in the light emitting layer, and the TTF phenomenon occurs. As a result, the fluorescent element is realized with high efficiency and long life.
- the electron injection property is improved, and the blue fluorescent light-emitting layer, green phosphorescent light-emitting layer, and red
- the relationship between the materials used for the electron transport layer provided in common with the phosphorescent light-emitting layer has been found, and high efficiency of the full-color element has been realized.
- JP-T-2002-525808 discloses a technique for improving efficiency by providing a barrier layer made of BCP (basocuproin) which is a phenanthroline derivative so as to be adjacent to the light emitting layer, and confining holes and excitons. Yes.
- BCP basic polypeptide
- a specific aromatic ring compound is used for a hole blocking layer to achieve high efficiency and long life.
- TTA triplet-triplet annihilation
- An object of the present invention is to improve efficiency and lifetime without increasing the manufacturing cost in an organic EL device having a blue light emitting layer, a green light emitting layer, and a red light emitting layer.
- the following organic EL elements are provided. 1. Between the anode and cathode facing each other, from the anode side, a hole transport zone, a light emitting layer and an electron transport zone are provided in this order, The light emitting layer is formed of a red light emitting layer, a green light emitting layer and a blue light emitting layer, The blue light emitting layer includes a host BH and a fluorescent light emitting dopant FBD, The triplet energy E T fbd of the fluorescent luminescent dopant FBD is greater than the triplet energy E T bh of the host BH; The green light emitting layer includes a host GH and a phosphorescent dopant PGD, In said electron transporting zone, the red light emitting layer, a common electron transport layer adjacent to the green light emitting layer and the blue light emitting layer is provided, the triplet energy E T el of the material constituting the electron transport layer is E Greater than T bh , The difference in affinity between the host a host BH and
- the red light emitting layer includes a host RH and a phosphorescent dopant PRD, 2.
- the organic electroluminescence device according to any one of 1 to 4, wherein an electron injection layer is provided between the electron transport layer and the cathode in the electron transport zone. 6).
- the organic electroluminescence device according to any one of 1 to 5, wherein the host GH has an affinity Af gh of 2.6 eV or more. 7).
- the organic electroluminescence device according to any one of 1 to 6, wherein an ionization potential Ip gd of the dopant GD is 5.2 eV or more. 8).
- the organic electroluminescence device according to any one of 1 to 7, wherein a second dopant is included in at least one of the blue light emitting layer, the green light emitting layer, and the red light emitting layer. 9.
- the efficiency and life can be improved without increasing the manufacturing cost.
- FIG. 1 is a diagram showing a configuration of an organic EL element according to an embodiment of the present invention.
- the organic EL element 1 includes a hole transport zone 20, a light emitting layer 30, and an electron transport zone 40 in this order from the anode 10 side between the anode 10 and the cathode 50 facing each other on the substrate 60.
- the light emitting layer 30 is formed of a blue light emitting layer 32, a green light emitting layer 34 and a red light emitting layer 36.
- the light emitting layer 30 is provided with a red light emitting layer 36, a green light emitting layer 34, and a blue light emitting layer 32 juxtaposed in a direction perpendicular to the substrate surface.
- the blue light emitting layer 32 includes a host BH and a fluorescent light emitting dopant FBD
- the green light emitting layer 34 includes a host GH and a phosphorescent light emitting dopant PGD
- the red light emitting layer 36 includes a host RH and phosphorescent light emitting material.
- a dopant PRD a common electron transport layer 42 is provided in the electron transport zone 40 adjacent to the blue light emitting layer 32, the green light emitting layer 34 and the red light emitting layer 36.
- An electron injection layer 44 is preferably provided in the electron transport zone 40 and between the electron transport layer 42 and the cathode 50, more preferably adjacent to the electron transport layer 42.
- a hole transport layer or a hole transport layer and a hole injection layer can be provided.
- the anode 10 is laminated on the substrate 60 and patterned.
- the anode 10 uses a metal film which is a reflective film in the case of a front light emitting structure, and indium tin oxide (ITO) or indium zinc oxide which is a transparent electrode in the case of a back light emitting structure.
- ITO indium tin oxide
- ITO indium zinc oxide
- a hole transport zone 20 a hole injection layer is laminated over the entire surface of the substrate, and a hole transport layer is further laminated thereon. Each light emitting layer is formed so as to correspond to the position of the anode.
- the blue light emitting layer 32, the green light emitting layer 34, and the red light emitting layer 36 are finely patterned using a shadow mask.
- the electron transport zone 40 is laminated over the entire surface of the blue light emitting layer 32, the green light emitting layer 34 and the red light emitting layer 36.
- a cathode is laminated to complete an organic EL element.
- the substrate a glass substrate, a TFT substrate, or the like can be used.
- the hole transport zone 20 is provided in common using a common material as the hole injection layer and the hole transport layer, but the blue light emitting layer 32, the green light emitting layer 34, and the red light emitting layer are provided.
- different materials may be provided by micropatterning.
- the hole transporting zone may be a single hole transporting layer, or two or more layers may be laminated by a combination of a hole injection layer and a hole transporting layer.
- some layers are provided in common, and the other layers correspond to the blue light emitting layer 32, the green light emitting layer 34, and the red light emitting layer 36, and different materials are used. It may be provided by forming a fine pattern.
- the light emitting layer of the organic EL element of the present invention includes a blue pixel, a green pixel, and a red pixel.
- the blue pixel is from the blue light emitting layer
- the green pixel is from the green light emitting layer
- the red pixel is from the red light emitting layer. Composed.
- a voltage is applied to each pixel independently. Therefore, in the organic EL element 1 of FIG. 1, the blue light emitting layer 32, the green light emitting layer 34, and the red light emitting layer 36 do not always emit light at the same time, but the three light emitting layers 32, 34, 36 are selectively made to emit light, respectively. be able to.
- the organic EL element of the present embodiment includes one blue pixel, one green pixel, and one red pixel, but may be repeated with these as one unit. Also, there may be a plurality of each pixel. For example, the repetition may be a single unit composed of one blue pixel, two green pixels, and one red pixel.
- the organic EL element of the present invention has a phenomenon described in Non-Patent Document 1, that is, a phenomenon in which singlet excitons are generated by collisional fusion of two triplet excitons (hereinafter, referred to as “blue light emitting layer 32”).
- Triplet-Triplet-Fusion TTF phenomenon).
- the TTF phenomenon will be described below. Holes and electrons injected from the anode and cathode recombine in the light emitting layer to generate excitons.
- the spin state has a ratio of 25% for singlet excitons and 75% for triplet excitons, as is conventionally known.
- TTF ratio TTF-derived emission ratio
- FIG. 2 is a schematic diagram showing an example of the energy level of the blue light emitting layer of the organic EL element shown in FIG.
- the upper diagram of FIG. 2 shows the device configuration and the HOMO and LUMO energy levels of each layer (the LUMO energy level may be referred to as affinity (Af), and the HOMO energy level may be referred to as ionization potential (Ip)).
- the following diagram schematically shows the lowest excited singlet energy level and the lowest excited triplet energy level of each layer.
- the triplet energy is the difference between the energy in the lowest excited triplet state and the energy in the ground state
- the singlet energy (sometimes referred to as an energy gap) is the lowest excited singlet state. The difference between energy and ground state energy.
- Holes injected from the anode are injected into the light emitting layer through the hole transport zone, and electrons injected from the cathode are injected into the light emitting layer through the electron transport zone. Thereafter, holes and electrons are recombined in the light emitting layer, and singlet excitons and triplet excitons are generated. There are two ways in which recombination occurs on the host molecule and on the dopant molecule. As shown in the lower diagram of FIG. 2, when the triplet energies of the host and dopant of the blue light emitting layer are E T h and E T d , respectively, the relationship of E T h ⁇ E T d is satisfied.
- triplet excitons generated by recombination on the host do not move to a dopant having a higher triplet energy. Further, triplet excitons generated by recombination on the dopant molecule quickly transfer energy to the host molecule. That is, triplet excitons collide with each other on the host efficiently by the TTF phenomenon without the triplet excitons of the host moving to the dopant, so that singlet excitons are generated. Furthermore, since the singlet energy E S d of the dopant is smaller than the singlet energy E S h of the host, singlet excitons generated by the TTF phenomenon transfer energy from the host to the dopant, and the fluorescence of the dopant. Contributes to light emission.
- the electron transport layer prevents triplet excitons generated in the blue light-emitting layer from diffusing into the electron transport band, and confines the triplet excitons in the blue light-emitting layer. It has the function of increasing the child density and causing the TTF phenomenon efficiently.
- triplet energy E T el of the electron transport layer is greater than E T h, further preferably larger than E T d. Since the electron transport layer prevents the triplet excitons from diffusing into the electron transport band, the host triplet excitons efficiently become singlet excitons in the blue light-emitting layer, and the singlet excitons thereof. The child moves onto the dopant and optically deactivates.
- the hole transport layer in the hole transport zone, is adjacent to the blue light-emitting layer, and the triplet energy E T ho of the hole transport layer is expressed as the E T of the host of the blue light-emitting layer.
- E T ho of the hole transport layer is expressed as the E T of the host of the blue light-emitting layer.
- the difference in affinity between the host GH of the green light emitting layer and the material constituting the electron transport layer is within 0.4 eV.
- the triplet energy of the phosphorescent dopant PGD green emitting layer is greater than the triplet energy E T el of the material constituting the electron transport layer. Therefore, it is preferable that the triplet energy E T el of the material forming the electron-transporting layer larger than the triplet energy of the phosphorescent dopant PGD.
- an electron transport material having a large triplet energy has problems in electron injection from an electrode and hole durability. In order to obtain an optimum phosphorescent device, an electron transport material having a large triplet energy.
- triplet excitons on the phosphorescent dopant PGD are transferred to a material constituting an electron transport layer having a smaller triplet energy before phosphorescence emission, and the light emission efficiency of the green light emission layer is lowered. . Therefore, as in the present invention, when the difference in affinity between the host GH of the green light emitting layer and the material constituting the electron transporting layer is within 0.4 eV, the electron injection property from the electron transporting layer to the green light emitting layer is improved. Electrons and holes are recombined with bias toward the hole transport band side of the light emitting layer, that is, away from the electron transport band.
- the hole mobility ⁇ h and the electron mobility ⁇ e of the host of the light emitting layer are preferably ⁇ e / ⁇ h> 1. Particularly preferably, ⁇ e / ⁇ h> 5.
- the light emitting layers of three colors are formed in parallel, but mass productivity is improved by using a common material as the electron transport layer.
- the blue light emitting layer uses the TTF phenomenon to increase the light emitting efficiency of the blue light emitting layer, and the green light emitting layer adjusts the affinity to prevent the light emitting efficiency of the green light emitting layer from being lowered, so Both have achieved high efficiency.
- the red light emitting layer 36 can be configured to include the host RH and the phosphorescent dopant PRD.
- the difference in affinity between the host RH and the material constituting the electron transport layer is preferably within 0.4 eV. This is because, as described above, it is difficult to transfer triplet energy from the red light emitting layer to the electron transporting layer to prevent a decrease in light emission efficiency.
- the difference in affinity between the host BH of the blue light emitting layer and the material constituting the electron transport layer is within 0.4 eV. This is because the electron injection property to the light emitting layer is improved by setting the difference in affinity within 0.4 eV.
- the electron injecting property to the light emitting layer is lowered, the density of triplet excitons is reduced by reducing electron-hole recombination in the light emitting layer.
- the collision frequency of triplet excitons decreases and the TTF phenomenon does not occur efficiently.
- the voltage can be lowered by improving the electron injection.
- the host GH preferably has an affinity Af gh of 2.6 eV or more in order to increase the inflow of electrons and separate the recombination region from the electron transport band.
- the ionization potential Ip gd of the dopant GD of the green light emitting layer is preferably 5.2 eV or more in order to improve the recombination probability.
- the green light emitting layer preferably includes a second dopant GD2 having an affinity Af gd2 having a difference from the affinity Af gh of the host GH within 0.4 eV . Furthermore, it is desirable that the energy gap of the dopant PGD is smaller than the energy gap of the second dopant GD2.
- electrons typically move from the electron transport layer to the host GH of the green light emitting layer, and then from the host GH to the dopant PGD.
- the difference between the affinity Af gh of the host GH and the affinity Af gd of the dopant increases and the electron injectability into the dopant decreases, a part of the electrons flows in the anode direction as it is without moving from the host GH to the dopant PGD. There is a case.
- the electrons are transferred from the electron transport layer to the host GH of the green light emitting layer, then the second dopant GD2, and the dopant PGD. It is possible to prevent some of the electrons from flowing to the anode without moving to the dopant PGD. Therefore, more electrons reach the dopant PGD and the recombination probability is improved, resulting in an increase in luminous efficiency.
- the blue light-emitting layer and the red light-emitting layer may also contain the second dopant having an affinity Af gd2 having a difference from the host affinity Af gh of 0.4 eV or less as described above.
- the second dopant By including the second dopant, it is possible to prevent electrons from flowing in the anode direction without moving to the dopant.
- the blue light-emitting layer, the green light-emitting layer, the host of the red light-emitting layer, the dopant, and the material constituting the electron transport layer are selected from known compounds, and the compounds satisfying the above-described conditions necessary for the present invention or suitable conditions. It can manufacture by selecting.
- the material of each layer is not limited as long as the conditions necessary for the present invention are satisfied, but is preferably selected from the following compounds.
- the host of the blue light emitting layer is an anthracene derivative, a polycyclic aromatic skeleton-containing compound or the like, preferably an anthracene derivative.
- the dopant of the blue light emitting layer is fluoranthene derivative, pyrene derivative, arylacetylene derivative, fluorene derivative, boron complex, perylene derivative, oxadiazole derivative, anthracene derivative, etc., preferably fluoranthene derivative, pyrene derivative, boron complex, more preferably Fluoranthene derivatives and boron complex compounds.
- the host is an anthracene derivative and the dopant is a fluoranthene derivative or a boron complex.
- X 1 to X 12 are hydrogen or a substituent.
- X 1 to X 2 , X 4 to X 6 and X 8 to X 11 are hydrogen atoms
- X 3 , X 7 and X 12 are substituted or unsubstituted aryl groups having 5 to 50 ring atoms. It is a compound which is.
- X 1 to X 2 , X 4 to X 6 and X 8 to X 11 are hydrogen atoms, and X 7 and X 12 are substituted or unsubstituted aryl groups having 5 to 50 ring atoms, X A compound in which 3 is —Ar 1 —Ar 2 (Ar 1 is a substituted or unsubstituted arylene group having 5 to 50 ring atoms, Ar 2 is a substituted or unsubstituted aryl group having 5 to 50 ring atoms) It is.
- X 1 to X 2 , X 4 to X 6 and X 8 to X 11 are hydrogen atoms, and X 7 and X 12 are substituted or unsubstituted aryl groups having 5 to 50 ring atoms,
- X 3 is —Ar 1 —Ar 2 —Ar 3 (Ar 1 and Ar 2 are each a substituted or unsubstituted arylene group having 5 to 50 ring atoms; Ar 3 is a substituted or unsubstituted ring atom number 5; ⁇ 50 aryl groups).
- a and A ′ represent an independent azine ring system corresponding to a 6-membered aromatic ring system containing at least one nitrogen
- X a and X b are each independently a substituent
- a and Xb may be linked to ring A and ring A ′, respectively, to form a fused ring with ring A and ring A ′, wherein the fused ring contains an aryl or heteroaryl substituent
- m and n each independently represents 0-4
- Z a and Z b each independently represent a halide, and 1, 2, 3, 4, 1 ′, 2 ′, 3 ′ and 4 ′.
- the azine ring is such that 1, 2, 3, 4, 1 ′, 2 ′, 3 ′ and 4 ′ are all carbon atoms, m and n are 2 or more, and X a and X b are It is a quinolinyl or isoquinolinyl ring which represents a substituent having 2 or more carbon atoms that are linked to form an aromatic ring.
- Z a and Z b are preferably fluorine atoms.
- Ar 001 is a substituted or unsubstituted condensed aromatic group having 10 to 50 ring carbon atoms.
- Ar 002 is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.
- X 001 to X 003 are each independently a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms, substituted or unsubstituted An alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted ring atom having 5 to 50 ring atoms.
- a, b and c are each an integer of 0 to 4.
- n is an integer of 1 to 3. When n is 2 or more, the numbers in [] may be the same or different.
- n is 1.
- a, b and c are 0.
- the fluorescent light-emitting dopant of the blue light-emitting layer is preferably a compound represented by the following formula.
- Ar 1 to Ar 6 are each an aryl group having 6 to 30 carbon atoms
- Ar 7 is an arylene group having 6 to 30 carbon atoms.
- Ar 1 to Ar 7 may be substituted, and the substituent is preferably an alkoxy group, a dialkylamino group, an alkyl group, a fluoroalkyl group, or a silyl group.
- m is 0 or 1
- n is 0 or 1.
- L 1 and L 2 are each an alkenylene group or a divalent aromatic hydrocarbon group.
- a dibenzofuran compound described in WO05 / 113531, JP2005-314239, a fluorene compound described in WO02 / 14244, and a benzanthracene compound described in WO08 / 145239 can also be used.
- JP2004-204238, WO05 / 108348, WO04 / 83162, WO09 / 845122, KR10-2008-79958, KR10-2007-115588, KR10-2010-24894, pyrene compounds described in WO04 / 44088 And anthracene compounds described in WO07 / 21117 can also be used.
- the host is preferably a compound in which a cyclic structure or a single atom is bonded to each other (including a ring structure and a single atom bond), and the bond is a single bond.
- Unpreferable examples include compounds having a carbon-carbon double bond other than a cyclic structure. This is because the triplet exciton energy generated on the host is not used for the TTF phenomenon and is consumed for the structural change of the double bond.
- the host of the green light emitting layer is preferably a compound represented by the following formula (1) or (2).
- Ar 6 , Ar 7 and Ar 8 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted group. Represents an aromatic heterocyclic group having 3 to 24 ring atoms.
- Ar 6 , Ar 7 and Ar 8 may have one or a plurality of substituents Y, and when there are a plurality of them, they may be the same or different, and Y is an alkyl group having 1 to 20 carbon atoms.
- X 1 , X 2 , X 3 and X 4 each independently represent O, S, N—R 1 or CR 2 R 3 , and o, p and q are 0 Or 1, s represents 1, 2 or 3.
- R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or an aralkyl having 7 to 24 carbon atoms.
- L 1 is a single bond, an alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, or a divalent group having 2 to 20 carbon atoms.
- L 2 is a single bond, an alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a divalent silyl group having 2 to 20 carbon atoms, A substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 24 ring carbon atoms, or a substituted or unsubstituted divalent aromatic group having 3 to 24 ring atoms and linked to Ar 8 by a carbon-carbon bond Represents a heterocyclic group.
- n represents 2, 3 or 4, and each forms a dimer, trimer or tetramer with L 3 as a linking group.
- L 3 is a single bond, an alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, or 2 to 20 carbon atoms.
- a 1 represents a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted ring formation. It represents an aromatic hydrocarbon group having 6 to 24 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 ring atoms and linked to L 1 by a carbon-carbon bond.
- a 2 is a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a silyl group having 3 to 20 carbon atoms, a substituted or unsubstituted ring carbon number 6 to 24 represents an aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 ring-forming atoms and linked to L 2 by a carbon-carbon bond.
- the host of the green light emitting layer is preferably a compound represented by the following general formula (3) or (4).
- (Cz-) n A (3) Cz (-A) m (4) [Wherein, Cz is a substituted or unsubstituted arylcarbazoyl group or carbazoylalkylene group, and A is a group represented by the following general formula.
- n and m are each an integer of 1 to 3.
- M and M ′ are each independently a nitrogen-containing heteroaromatic ring having 2 to 40 carbon atoms that forms a substituted or unsubstituted ring, and may be the same or different.
- L is a single bond or a substituted ring.
- an unsubstituted arylene group having 6 to 30 carbon atoms a substituted or unsubstituted cycloalkylene group having 5 to 30 carbon atoms, and a substituted or unsubstituted heteroaromatic ring having 2 to 30 carbon atoms, p being 0 to 2
- q is an integer from 1 to 2
- r is an integer from 0 to 2, provided that p + r is 1 or more.
- the phosphorescent dopant of the green light-emitting layer preferably contains a metal complex composed of a metal selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and Ru and a ligand.
- a metal complex composed of a metal selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and Ru and a ligand.
- Specific examples of such a dopant material include, for example, PQIr (iridium (III) bis (2-phenylquinolyl-N, C 2 ′ ) acetylacetonate), Ir (ppy) 3 (fac-tris (2-phenylpyridine) iridium).
- PQIr iridium (III) bis (2-phenylquinolyl-N, C 2 ′ ) acetylacetonate
- Ir (ppy) 3 fac-tris (2-phenylpyridine) iridium
- the second dopant a material that can be used as a host material of the green light-emitting layer can be used. Therefore, the example of the 2nd dopant of a green light emitting layer is the same as the exemplary compound of the host of said green light emitting layer.
- the second dopant is preferably selected to have an affinity Af gd2 having a difference from the affinity Af gh of the host GH within 0.4 eV . Furthermore, it is desirable to select an energy gap of the dopant PGD that is smaller than the energy gap of the second dopant GD2.
- the host of the red light emitting layer is, for example, one or more compounds selected from the group consisting of polycyclic condensed aromatic compounds represented by the following formulas (A), (B), and (C).
- Ar 101 , Ar 102 , Ar 103 , Ra and Rb are each independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted chrysene ring, a substituted Or an unsubstituted fluoranthene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzophenanthrene ring, a substituted or unsubstitute
- Ra and Rb is preferably a ring selected from the group consisting of a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted benzo [c] phenanthrene ring and a substituted or unsubstituted fluoranthene ring.
- the polycyclic fused aromatic skeleton is contained in the chemical structural formula as a divalent or higher valent group.
- the polycyclic aromatic skeleton may have a substituent, and the substituent is, for example, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.
- the substituent of the polycyclic fused aromatic compound is, for example, a group that does not have a carbazole skeleton.
- the phosphorescent dopant of the red light-emitting layer preferably contains a metal complex composed of a metal selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and Ru and a ligand.
- a metal complex composed of a metal selected from the group consisting of Ir, Pt, Os, Au, Cu, Re, and Ru and a ligand.
- the material used for the electron transport layer is preferably a material having excellent oxidation durability.
- a material excellent in oxidation durability a hydrocarbon aromatic compound, particularly a condensed polycyclic aromatic ring compound is preferable.
- An organic complex such as BAlq has polarity in the molecule and is inferior in oxidation resistance.
- the electron transport zone is composed of one or more electron transport layers, or a stack of one or more electron transport layers and one or more electron injection layers.
- the configuration between the light emitting layer and the cathode is as follows. Light emitting layer / electron transport layer / cathode light emitting layer / electron transport layer / electron injection layer / cathode light emitting layer / electron transport layer / electron transport layer / electron injection layer / cathode
- the electron transport region is provided in common for the green light emitting layer, the blue light emitting layer, and the red light emitting layer. Therefore, the triplet energy of the material composing the electron transport layer adjacent to the light emitting layer is larger than the triplet energy of the host of the blue light emitting layer, and the host transport layer adjacent to the light emitting layer constitutes the affinity of the host of the green light emitting layer.
- the difference in the affinity of the materials to be used may be within 0.4 eV.
- the difference between the affinity of the host of the red light emitting layer and the affinity of the material constituting the electron transport layer adjacent to the light emitting layer is preferably within 0.4 eV.
- the difference between the affinity of the host of the blue light emitting layer and the affinity of the material constituting the electron transport layer adjacent to the light emitting layer is preferably within 0.4 eV.
- the material constituting the electron transport layer are selected from the group consisting of the polycyclic fused aromatic compounds of (10), (20) and (30) below. One or more compounds may be mentioned.
- R 1 to R 21 represent a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a halogen atom, a nitro group, a cyano group, or a hydroxyl group.
- X represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group.
- HAr is a nitrogen-containing heterocycle having 3 to 40 carbon atoms which may have a substituent
- L 1 is a single bond or an arylene having 6 to 40 carbon atoms which may have a substituent.
- Ar 1 is a divalent aromatic hydrocarbon group having 6 to 40 carbon atoms which may have a substituent.
- Ar 2 is an aryl group having 6 to 40 carbon atoms which may have a substituent or a heteroaryl group having 3 to 40 carbon atoms which may have a substituent.
- Ar 1 is preferably an anthracenylene group in relation to the affinity of the light emitting layer host material.
- it is preferable that it is a compound represented by (12) from a heat resistant viewpoint.
- the electron transport layer and the electron injection layer that do not contact the light-emitting layer are preferably a metal complex of 8-hydroxyquinoline or a derivative thereof, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative.
- a metal complex of the above 8-hydroxyquinoline or a derivative thereof a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used.
- a metal chelate oxinoid compound containing a chelate of oxine generally 8-quinolinol or 8-hydroxyquinoline
- tris (8-quinolinol) aluminum is used.
- nitrogen-containing heterocyclic derivative examples include the above compound (20).
- the mobility of the material constituting the electron transport layer is preferably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm. More desirably, it is 10 ⁇ 4 cm 2 / Vs or more.
- a method for measuring the electron mobility of an organic material several methods such as the Time of Flight method are known. In the present invention, the electron mobility is determined by impedance spectroscopy.
- the mobility measurement by impedance spectroscopy will be described.
- An electron transport layer material having a thickness of preferably about 100 nm to 200 nm is sandwiched between the anode and the cathode, and a minute AC voltage of 100 mV or less is applied while applying a bias DC voltage.
- the AC current value (absolute value and phase) flowing at this time is measured. This measurement is performed while changing the frequency of the AC voltage, and the complex impedance (Z) is calculated from the current value and the voltage value.
- Electron mobility (film thickness of electron transport layer material) 2 / (response time / voltage)
- a material having an electron mobility of 10 ⁇ 6 cm 2 / Vs or more in an electric field strength of 0.04 to 0.5 MV / cm a material having a fluoranthene derivative in a polycyclic aromatic skeleton is given. Can do.
- the electron transport zone a stack of the above-described electron transport material and an alkali metal compound, or a material in which an electron transport layer is formed and a donor typified by an alkali metal or the like is added can be used.
- the alkali metal compound include alkali metal halides and oxides. More preferred is an alkali metal fluoride. For example, LiF is preferably used.
- the affinity Ae of the electron injection layer ⁇ the affinity Ab of the electron transport layer ⁇ 0.2 eV. If this is not satisfied, electron injection from the electron injection layer to the electron transport layer is impaired, electrons are accumulated in the electron transport band, causing a high voltage, and the accumulated electrons collide with triplet excitons and energy. May be quenched.
- the electron transport layer is preferably made of a barrier material having an electron transport structure portion and a triplet barrier structure portion made of a condensed polycyclic aromatic hydrocarbon compound.
- the structural moiety is an individual cyclic structure (monocyclic or condensed polycyclic excluding substituents) contained in the compound.
- the triplet barrier structure site refers to a structure site having the lowest (smallest) triplet energy among the structure sites contained in the compound. That is, it is a structural site that mainly determines the triplet energy of the compound. There may be a plurality of triplet barrier structure sites.
- the triplet energy of the triplet barrier structure site refers to the triplet energy of an independent cyclic structure in which hydrogen is substituted at the bonding position of each structure site except for the substituent.
- the hole transport layer contains an aromatic amine derivative represented by any of the following formulas (1) to (5).
- Ar 1 to Ar 24 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- L 1 to L 9 each independently represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- the substituents that Ar 1 to Ar 24 and L 1 to L 9 may have include a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, carbon
- An alkylarylsilyl group having an alkyl group and an aryl group having 6 to 14 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms, a heteroaryl group having 5 to 50 ring atoms, a halogen atom or a cyano group is there.
- a plurality of adjacent substituents may be bonded to each other to form a saturated or unsaturated divalent group forming a ring.
- At least one of Ar 1 to Ar 24 is a substituent represented by any of the following formulas (6) and (7).
- X represents an oxygen atom, a sulfur atom, or N—Ra
- Ra represents a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, It represents an aryl group having 6 to 50 ring carbon atoms or a heteroaryl group having 5 to 50 ring atoms.
- L 10 represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- L 11 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- R 1 to R 4 are each independently a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, a straight chain having 1 to 15 carbon atoms, A trialkylsilyl group having a branched alkyl group, a triarylsilyl group having an aryl group having 6 to 14 ring carbon atoms, a linear or branched alkyl group having 1 to 15 carbon atoms, and a ring carbon number of 6 An alkylarylsilyl group having an aryl group of ⁇ 14, an aryl group having 6 to 14 ring carbon atoms, a heteroaryl group having 5 to 50 ring atoms, a halogen atom or a
- the compound represented by the formula (1) is a compound represented by the following formula (8).
- Cz represents a substituted or unsubstituted carbazolyl group.
- L 12 represents a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- Ar 25 and Ar 26 each independently represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- the compound represented by the formula (8) is preferably a compound represented by the following formula (9).
- R 5 and R 6 are each independently a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, or a C 1 to 15 carbon atoms.
- a plurality of R 5 and R 6 may be bonded to each other to form a ring.
- e and f each represents an integer of 0 to 4.
- L 12, Ar 25 and Ar 26 are the same meaning as L 12, Ar 25 and Ar 26 in the formula (8). )
- the compound represented by the formula (9) is preferably a compound represented by the following formula (10).
- R 7 and R 8 are each independently a linear or branched alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 3 to 15 ring carbon atoms, or a C 1 to 15 carbon atoms.
- R 5 and R 6 may be bonded to each other to form a ring.
- g and h each represents an integer of 0 to 4.
- R 5, R 6, e, f, Ar 25 and Ar 26 are the same meaning as R 5, R 6, e, f, Ar 25 and Ar 26 in the formula (9). )
- the measuring method of physical properties is as follows.
- (1) Triplet energy (E T ) The measurement was performed using a commercially available apparatus F-4500 (manufactured by Hitachi).
- Conversion formula of E T is as follows.
- the ionization potential was measured using an atmospheric photoelectron spectrometer (manufactured by Riken Keiki Co., Ltd .: AC-1). Specifically, the measurement was performed by irradiating the material with light and measuring the amount of electrons generated by charge separation at that time.
- the measured value of the energy gap was subtracted from the ionization potential.
- the energy gap was measured from the absorption edge of the absorption spectrum in benzene. Specifically, the absorption spectrum was measured using a commercially available visible / ultraviolet spectrophotometer, and calculated from the wavelength at which the spectrum started to rise.
- Example 1 The material which comprises the following layer was vapor-deposited sequentially on the board
- Anode ITO (130 nm thickness)
- the blue light emitting layer, the green light emitting layer, and the red light emitting layer of the obtained device were made to emit light with a direct current of 1 mA / cm 2 , and the light emission efficiency (unit: cd / A) was measured. Further, initial luminance blue: 5,000 cd / m 2, green 20,000 cd / m 2, the half-life subjected to a DC continuous current test with red 10,000cd / m 2 (unit: hour) was measured. The results are shown in Table 1.
- Examples 2-5 Comparative Example 1 An organic EL device was obtained and evaluated in the same manner as in Example 1 except that the blue light-emitting layer, red light-emitting layer, green light-emitting layer host, dopant, and electron transport layer shown in Table 1 were used. The results are shown in Table 1.
- the green light emitting layer of Example 5 added the 2nd dopant as shown in Table 1.
- the concentration of the second dopant GH_10 was 20 wt%
- the concentration of the first dopant Ir (ppy) 3 was 10 wt%.
- Example 6 The material which comprises the following layer was vapor-deposited sequentially on the board
- the obtained organic EL device was evaluated in the same manner as in Example 1. The results are shown in Table 1.
- Anode ITO (130 nm thickness)
- Hole injection layer HI (film thickness 50 nm)
- Hole transport layer HT (film thickness 45 nm)
- Light emitting layer (film thickness blue 25nm, green 50nm, red 40nm)
- RH_1 Ir (piq) 3 (10 wt%)
- Electron transport layer ET2 (film thickness 5 nm)
- LiF (film thickness 1 nm)
- Cathode Al (film thickness 80 nm)
- Example 7 to 27, Comparative Example 2 An organic EL device was obtained and evaluated in the same manner as in Example 6 except that the blue light emitting layer, red light emitting layer, green light emitting layer host, dopant, electron transport layer, and electron injection layer shown in Table 1 were used. The results are shown in Table 1. As shown in Table 1, the second dopant was added to the green light emitting layers of Examples 10, 15, 16, 21, 22, and 27. The concentration of the second dopant was 20 wt%, and the concentration of the first dopant was 10 wt%.
- the organic EL device of the present invention can be used for a display panel, a lighting panel, etc. for a large TV.
Abstract
Description
正孔抑制層を共通層とすることによって製造工程を減らしているが、正孔抑制層を共通層として用いたことによって、正孔障壁層から各発光層への電子注入が課題となっていた。実際に、青色発光層と正孔抑制層とのアフィニティの差は0.2eV程度と小さいが、緑色発光層にCBPのようなアフィニティの小さい材料を用いているため、正孔抑制層とのアフィニティの差が大きく、0.6eV程度となっている。このため緑色発光層において電子注入性が低下し、駆動電圧が高くなっている。さらに、緑色燐光発光層と正孔抑制層の界面に結合領域が集中するために、励起子の拡散が大きく緑色発光層の発光効率が上がらなかった。
また、フルカラー素子における、青色蛍光発光層、緑色燐光発光層及び赤色燐光発光層のそれぞれのホストのアフィニティの関係に着目し、電子注入性を改善し、青色蛍光発光層、緑色燐光発光層及び赤色燐光発光層に共通して設けられる電子輸送層に用いられる材料の関係を見出し、フルカラー素子の高効率化を実現するに至った。
1.対向する陽極と陰極の間に、陽極側から、正孔輸送帯域と発光層と電子輸送帯域とをこの順に備え、
前記発光層は、赤色発光層、緑色発光層及び青色発光層から形成され、
前記青色発光層は、ホストBHと蛍光発光性ドーパントFBDとを含み、
前記蛍光発光性ドーパントFBDの3重項エネルギーET fbdが前記ホストBHの3重項エネルギーET bhより大きく、
前記緑色発光層は、ホストGHと燐光発光性ドーパントPGDとを含み、
前記電子輸送帯域内に、前記赤色発光層、緑色発光層及び青色発光層に隣接して共通の電子輸送層が設けられ、前記電子輸送層を構成する材料の3重項エネルギーET elがET bhより大きく、
前記ホストGHと前記電子輸送層を構成する材料のアフィニティの差が0.4eV以内である、
有機エレクトロルミネッセンス素子。
2.前記赤色発光層は、ホストRHと燐光発光性ドーパントPRDとを含み、
前記ホストRHと前記電子輸送層を構成する材料のアフィニティの差が0.4eV以内である1に記載の有機エレクトロルミネッセンス素子。
3.前記ホストBHと前記電子輸送層を構成する材料のアフィニティの差が0.4eV以内である1又は2に記載の有機エレクトロルミネッセンス素子。
4.前記電子輸送層を構成する材料の電子移動度が、電界強度0.04~0.5MV/cmの範囲において10-6cm2/Vs以上である1乃至3のいずれかに記載の有機エレクトロルミネッセンス素子。
5.前記電子輸送帯域内に、前記電子輸送層と前記陰極の間に電子注入層が設けられている1乃至4のいずれかに記載の有機エレクトロルミネッセンス素子。
6.前記ホストGHのアフィニティAfghが2.6eV以上である1乃至5のいずれかに記載の有機エレクトロルミネッセンス素子。
7.前記ドーパントGDのイオン化ポテンシャルIpgdが5.2eV以上である1乃至6のいずれかに記載の有機エレクトロルミネッセンス素子。
8.前記青色発光層、前記緑色発光層、前記赤色発光層のうち少なくとも一つの発光層に第二ドーパントを含む1乃至7のいずれかに記載の有機エレクトロルミネッセンス素子。
9.前記緑色発光層が第二ドーパントGD2を含む8に記載の有機エレクトロルミネッセンス素子。
10.前記第二ドーパントGD2のアフィニティAfgd2と前記ホストGHのアフィニティAfghの差が0.4eV以内である9に記載の有機エレクトロルミネッセンス素子。
11.前記ホストBHが環式構造以外に二重結合を含まない化合物である1乃至10のいずれかに記載の有機エレクトロルミネッセンス素子。
図1は、本発明の一実施形態にかかる有機EL素子の構成を示す図である。
有機EL素子1は、基板上60の対向する陽極10と陰極50の間に、陽極10側から、正孔輸送帯域20と発光層30と電子輸送帯域40とをこの順に備える。
発光層30は、青色発光層32、緑色発光層34及び赤色発光層36から形成される。前記発光層30は、基板面に対し垂直方向に、赤色発光層36、緑色発光層34、青色発光層32が並置して設けられる。青色発光層32は、ホストBHと蛍光発光性ドーパントFBDとを含み、緑色発光層34は、ホストGHと燐光発光性ドーパントPGDとを含み、好ましくは赤色発光層36は、ホストRHと燐光発光性ドーパントPRDとを含む。
さらに、電子輸送帯域40内に、青色発光層32、緑色発光層34及び赤色発光層36に隣接して共通の電子輸送層42が設けられる。好ましくは電子輸送帯域40内であって電子輸送層42と陰極50との間に、より好ましくは電子輸送層42に隣接して電子注入層44が設けられる。
正孔輸送帯域20には、正孔輸送層、又は正孔輸送層及び正孔注入層を設けることができる。
各発光層を、陽極の位置に対応して配置するように形成する。真空蒸着法を用いる場合、青色発光層32、緑色発光層34及び赤色発光層36をシャドウマスクを用いて微細パターン化する。
次に、電子輸送帯域40を青色発光層32、緑色発光層34及び赤色発光層36の全面にかけて積層する。
次に、陰極を積層し、有機EL素子が完成する。
基板としてはガラス基板又はTFT基板等を用いることができる。
陽極、陰極から注入された正孔、電子は発光層内で再結合し励起子を生成する。そのスピン状態は、従来から知られているように、1重項励起子が25%、3重項励起子が75%の比率である。従来知られている蛍光素子においては、25%の1重項励起子が基底状態に緩和するときに光を発するが、残りの75%の3重項励起子については光を発することなく熱的失活過程を経て基底状態に戻る。従って、従来の蛍光素子の内部量子効率の理論限界値は25%といわれていた。
3A*+3A*→(4/9)1A+(1/9)1A*+(13/9)3A*
即ち、53A*→41A+1A*となり、当初生成した75%の3重項励起子のうち、1/5即ち20%が1重項励起子に変化することが予測されている。従って、光として寄与する1重項励起子は当初生成する25%分に75%×(1/5)=15%を加えた40%ということになる。このとき、全発光強度中に占めるTTF由来の発光比率(TTF比率)は、15/40、すなわち37.5%となる。また、当初生成した75%の3重項励起子のお互いが衝突して1重項励起子が生成した(2つの3重項励起子から1つの1重項励起子が生成した)とすると、当初生成する1重項励起子25%分に75%×(1/2)=37.5%を加えた62.5%という非常に高い内部量子効率が得られることとなる。このとき、TTF比率は37.5/62.5=60%となる。
図2の上図は、素子構成及び各層のHOMO、LUMOエネルギー準位を表す(尚、LUMOエネルギー準位はアフィニティ(Af)、HOMOエネルギー準位はイオン化ポテンシャル(Ip)という場合がある)である。下図は各層の最低励起1重項エネルギー準位及び最低励起3重項エネルギー準位を模式的に表す。なお、本発明で3重項エネルギーは、最低励起3重項状態におけるエネルギーと基底状態におけるエネルギーの差をいい、1重項エネルギーは(エネルギーギャップという場合もある)、最低励起1重項状態におけるエネルギーと基底状態におけるエネルギーの差をいう。
通常、緑色発光層の燐光発光性ドーパントPGDの3重項エネルギーは、電子輸送層を構成する材料の3重項エネルギーET elより大きい。従って、電子輸送層を構成する材料の3重項エネルギーET elを燐光発光性ドーパントPGDの3重項エネルギーより大きくすることが好ましい。しかしながら、3重項エネルギーの大きい電子輸送材料は、電極からの電子注入や正孔耐久性において課題を有しており、最適な燐光素子を得るためには、3重項エネルギーの大きい電子輸送材料を必ずしも採用できない。この場合、燐光発光性ドーパントPGD上の3重項励起子は、燐光発光前に、3重項エネルギーがより小さい電子輸送層を構成する材料に移り、緑色発光層の発光効率が低下してしまう。そこで、本発明のように、緑色発光層のホストGHと電子輸送層を構成する材料のアフィニティの差を0.4eV以内とすると、電子輸送層から緑色発光層への電子注入性が向上するため、電子と正孔が、発光層の正孔輸送帯域側に、即ち、電子輸送帯域から離れて偏って再結合する。その結果、3重項励起子が緑色発光層から離れて発生するため、3重項励起子エネルギーが緑色発光層から電子輸送層に移りにくくなり、発光効率の低下を防ぐことができる。
さらに、再結合領域を電子輸送層から遠ざける観点から、発光層のホストの正孔移動度μh及び電子移動度μeはμe/μh>1が望ましい。特に望ましくはμe/μh>5である。
上記に記載したドーパントの他、JP2004-204238,WO05/108348,WO04/83162,WO09/84512,KR10-2008-79956,KR10-2007-115588,KR10-2010-24894記載のピレン化合物、WO04/44088記載のクリセン化合物、WO07/21117記載のアントラセン化合物も使用できる。
式(2)において、L3は、nが2の場合、単結合、炭素数1~20のアルキレン基、置換若しくは無置換の環形成炭素数3~20のシクロアルキレン基、炭素数2~20の2価のシリル基、置換若しくは無置換の環形成炭素数6~24の2価の芳香族炭化水素基、又は環形成原子数3~24でAr8と炭素-炭素結合で連結する置換若しくは無置換の2価の芳香族複素環基を表し、nが3の場合、炭素数1~20の3価のアルカン、置換若しくは無置換の環形成炭素数3~20の3価のシクロアルカン、炭素数1~20の3価のシリル基、置換若しくは無置換の環形成炭素数6~24の3価の芳香族炭化水素基、又は環形成原子数3~24でAr8と炭素-炭素結合で連結する置換若しくは無置換の3価の芳香族複素環基を表し、nが4の場合、炭素数1~20の4価のアルカン、置換若しくは無置換の環形成炭素数3~20の4価のシクロアルカン、ケイ素原子、置換若しくは無置換の環形成炭素数6~24の4価の芳香族炭化水素基、又は環形成原子数3~24でAr8と炭素-炭素結合で連結する置換若しくは無置換の4価の芳香族複素環基を表す。
(Cz-)nA (3)
Cz(-A)m (4)
〔式中、Czは、置換もしくは無置換のアリールカルバゾイル基又はカルバゾイルアルキレン基、Aは、下記一般式で表される基である。n、mは、それぞれ1~3の整数である。
(M)p-(L)q-(M’)r
(M及びM’は、それぞれ独立に、置換もしくは無置換の環を形成する炭素数2~40の窒素含有ヘテロ芳香族環であり、同一でも異なっていてもよい。Lは、単結合、置換もしくは無置換の炭素数6~30のアリーレン基、置換もしくは無置換の炭素数5~30のシクロアルキレン基、置換もしくは無置換の炭素数2~30のヘテロ芳香族環である。pは0~2、qは1~2、rは0~2の整数である。ただし、p+rは1以上である。)〕
このようなドーパント材料の具体例としては、例えば、PQIr(iridium(III)bis(2-phenylquinolyl-N,C2’)acetylacetonate)、Ir(ppy)3(fac-tris(2-phenylpyridine)iridium)の他、下記の化合物が挙げられる。
第2のドーパントは、ホストGHのアフィニティAfghとの差が0.4eV以内のアフィニティAfgd2を有するものを選択することが好ましい。さらに、ドーパントPGDのエネルギーギャップは、第二ドーパントGD2のエネルギーギャップに比べて小さいものを選択することが望ましい。
Ra-Ar101-Rb ・・・(A)
Ra-Ar101-Ar102-Rb ・・・(B)
Ra-Ar101-Ar102-Ar103-Rb ・・・(C)
(式中、Ar101,Ar102,Ar103,Ra及びRbは、それぞれ独立して、置換若しくは無置換のベンゼン環、又は、置換若しくは無置換のナフタレン環、置換若しくは無置換のクリセン環、置換若しくは無置換のフルオランテン環、置換若しくは無置換のフェナントレン環、置換若しくは無置換のベンゾフェナントレン環、置換若しくは無置換のジベンゾフェナントレン環、置換若しくは無置換のトリフェニレン環、置換若しくは無置換のベンゾ[a]トリフェニレン環、置換若しくは無置換のベンゾクリセン環、置換若しくは無置換のベンゾ[b]フルオランテン環、及び、置換若しくは無置換のピセン環から選択される多環式縮合芳香族骨格部を表す。但し、Ar101,Ar102,Ar103,Ra及びRbが同時に置換若しくは無置換のベンゼン環である場合はない。)
また、多環式縮合芳香族化合物の置換基は、例えばカルバゾール骨格を有しない基である。
酸化耐久性に優れる材料の具体例としては、炭化水素芳香族化合物、特に縮合多環芳香族環化合物が好ましい。BAlqのような有機錯体は分子内に極性をもち酸化耐性に劣る。
発光層と陰極の間は、例えば以下のように構成される。
発光層/電子輸送層/陰極
発光層/電子輸送層/電子注入層/陰極
発光層/電子輸送層/電子輸送層/電子注入層/陰極
赤色発光層のホストのアフィニティと発光層に隣接する電子輸送層を構成する材料のアフィニティの差が0.4eV以内であることが好ましい。
青色発光層のホストのアフィニティと発光層に隣接する電子輸送層を構成する材料のアフィニティの差が0.4eV以内であることが好ましい。
-0.3eV<(発光層に隣接する電子輸送層のアフィニティ)-(緑色発光層のホストのアフィニティ)<0.4
-0.2eV<(発光層に隣接する電子輸送層のアフィニティ)-(緑色発光層のホストのアフィニティ)<0.4
HAr-L1-Ar1-Ar2
式中、HArは、置換基を有していてもよい炭素数3~40の含窒素複素環であり、L1は単結合、置換基を有していてもよい炭素数6~40のアリーレン基又は置換基を有していてもよい炭素数3~40のヘテロアリーレン基であり、Ar1は置換基を有していてもよい炭素数6~40の2価の芳香族炭化水素基であり、Ar2は置換基を有していてもよい炭素数6~40のアリール基又は置換基を有していてもよい炭素数3~40のヘテロアリール基である。
有機材料の電子移動度の測定方法としては、Time of Flight法等幾つかの方法が知られているが、本発明ではインピーダンス分光法で決定される電子移動度をいう。
度を算出する。
電子移動度=(電子輸送層材料の膜厚)2/(応答時間・電圧)
アルカリ金属化合物としては、アルカリ金属のハロゲン化物、酸化物が好ましいものとして挙げられる。さらに好ましくはアルカリ金属のフッ化物が好ましい。例えばLiFが好ましいものとして用いられる。
L1~L9は、各々独立して、置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基を表わす。
Ar1~Ar24、L1~L9が有してもよい置換基は、炭素数1~15の直鎖状もしくは分岐状のアルキル基、環形成炭素数3~15のシクロアルキル基、炭素数1~15の直鎖状もしくは分岐状のアルキル基を有するトリアルキルシリル基、環形成炭素数6~14のアリール基を有するトリアリールシリル基、炭素数1~15の直鎖状もしくは分岐状のアルキル基及び環形成炭素数6~14のアリール基を有するアルキルアリールシリル基、環形成炭素数6~50のアリール基、環形成原子数5~50のヘテロアリール基、ハロゲン原子又はシアノ基である。隣接した複数の置換基は、互いに結合して、環を形成する飽和もしくは不飽和の2価の基を形成してもよい。)
L10は、単結合、置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基を表わす。
L11は、置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基を表わす。
R1~R4は、各々独立して、炭素数1~15の直鎖状もしくは分岐状のアルキル基、環形成炭素数3~15のシクロアルキル基、炭素数1~15の直鎖状もしくは分岐状のアルキル基を有するトリアルキルシリル基、環形成炭素数6~14のアリール基を有するトリアリールシリル基、炭素数1~15の直鎖状もしくは分岐状のアルキル基及び環形成炭素数6~14のアリール基を有するアルキルアリールシリル基、環形成炭素数6~14のアリール基、環形成原子数5~50のヘテロアリール基、ハロゲン原子又はシアノ基を表す。また、隣接した複数のR1~R4は互いに結合して環を形成してもよい。
a、c、dは0~4の整数を表わす。
bは0~3の整数を表わす。)
L12は置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基を表わす。
Ar25及びAr26は、各々独立して、置換もしくは無置換の環形成炭素数6~50のアリール基、又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基を表わす。)
e、fは0~4の整数を表わす。
L12、Ar25及びAr26は、式(8)におけるL12、Ar25及びAr26と同義である。)
g、hは0~4の整数を表わす。
R5、R6、e、f、Ar25及びAr26は、式(9)におけるR5、R6、e、f、Ar25及びAr26と同義である。)
(1)3重項エネルギー(ET)
市販の装置F-4500(日立社製)を用いて測定した。ETの換算式は以下の通りである。
換算式 ET(eV)=1239.85/λedge
「λedge」とは、縦軸にりん光強度、横軸に波長をとって、りん光スペクトルを表したときに、りん光スペクトルの短波長側の立ち上がりに対して接線を引き、その接線と横軸の交点の波長値を意味する。単位:nm。
大気下光電子分光装置(理研計器(株)社製:AC-1)を用いて測定した。具体的には、材料に光を照射し、その際に電荷分離によって生じる電子量を測定することにより測定した。
イオン化ポテンシャルからエネルギーギャップの測定値を差し引いた。エネルギーギャップはベンゼン中の吸収スペクトルの吸収端から測定した。具体的には、市販の可視・紫外分光光度計を用いて、吸収スペクトルを測定し、そのスペクトルが立ち上がり始める波長から算出した。
膜厚130nmのITOが成膜された基板上に、下記層を構成する材料を順次蒸着し、有機EL素子を得た。
陽極: ITO(膜厚130nm)
正孔注入層:HI(膜厚50nm)
正孔輸送層:HT(膜厚45nm)
発光層:(膜厚 青25nm,緑50nm,赤40nm)
青色発光層BH_1:BD_1(5wt%)、緑色発光層GH_1:Ir(Ph-ppy)3(10wt%)、赤色発光層RH_1:Ir(piq)3(10wt%)
電子輸送層(ETL):ET1(膜厚5nm)
LiF:(膜厚1nm)
陰極: Al(膜厚80nm)
表1に示す青色発光層、赤色発光層、緑色発光層のホスト、ドーパント、電子輸送層を用いた他は、実施例1と同様にして有機EL素子を得て、評価した。結果を表1に示す。
尚、実施例5の緑色発光層は、表1に示すように、第2のドーパントを追加した。第2のドーパントGH_10の濃度は20wt%、第1のドーパントIr(ppy)3の濃度は10wt%であった。
膜厚130nmのITOが成膜された基板上に、下記層を構成する材料を順次蒸着し、有機EL素子を得た。得られた有機EL素子を実施例1と同様にして評価した。結果を表1に示す。
陽極: ITO(膜厚130nm)
正孔注入層:HI(膜厚50nm)
正孔輸送層:HT(膜厚45nm)
発光層:(膜厚 青25nm,緑50nm,赤40nm)
青色発光層BH_2:BD_2(5wt%)、緑色発光層GH_1:Ir(ppy)3(10wt%)、赤色発光層RH_1:Ir(piq)3(10wt%)
電子輸送層(ETL):ET2(膜厚5nm)
電子注入層(EIL):EI1(膜厚20nm)
LiF:(膜厚1nm)
陰極: Al(膜厚80nm)
表1に示す青色発光層、赤色発光層、緑色発光層のホスト、ドーパント、電子輸送層、電子注入層を用いた他は、実施例6と同様にして有機EL素子を得て、評価した。結果を表1に示す。
尚、実施例10,15,16,21,22,27の緑色発光層は、表1に示すように、第2のドーパントを追加した。第2のドーパントの濃度は20wt%、第1のドーパントの濃度は10wt%であった。
Claims (11)
- 対向する陽極と陰極の間に、陽極側から、正孔輸送帯域と発光層と電子輸送帯域とをこの順に備え、
前記発光層は、赤色発光層、緑色発光層及び青色発光層から形成され、
前記青色発光層は、ホストBHと蛍光発光性ドーパントFBDとを含み、
前記蛍光発光性ドーパントFBDの3重項エネルギーET fbdが前記ホストBHの3重項エネルギーET bhより大きく、
前記緑色発光層は、ホストGHと燐光発光性ドーパントPGDとを含み、
前記電子輸送帯域内に、前記赤色発光層、緑色発光層及び青色発光層に隣接して共通の電子輸送層が設けられ、前記電子輸送層を構成する材料の3重項エネルギーET elがET bhより大きく、
前記ホストGHと前記電子輸送層を構成する材料のアフィニティの差が0.4eV以内である、
有機エレクトロルミネッセンス素子。 - 前記赤色発光層は、ホストRHと燐光発光性ドーパントPRDとを含み、
前記ホストRHと前記電子輸送層を構成する材料のアフィニティの差が0.4eV以内である請求項1に記載の有機エレクトロルミネッセンス素子。 - 前記ホストBHと前記電子輸送層を構成する材料のアフィニティの差が0.4eV以内である請求項1又は2に記載の有機エレクトロルミネッセンス素子。
- 前記電子輸送層を構成する材料の電子移動度が、電界強度0.04~0.5MV/cmの範囲において10-6cm2/Vs以上である請求項1乃至3のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記電子輸送帯域内に、前記電子輸送層と前記陰極の間に電子注入層が設けられている請求項1乃至4のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記ホストGHのアフィニティAfghが2.6eV以上である請求項1乃至5のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記ドーパントGDのイオン化ポテンシャルIpgdが5.2eV以上である請求項1乃至6のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記青色発光層、前記緑色発光層、前記赤色発光層のうち少なくとも一つの発光層に第二ドーパントを含む請求項1乃至7のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記緑色発光層が第二ドーパントGD2を含む請求項8に記載の有機エレクトロルミネッセンス素子。
- 前記第二ドーパントGD2のアフィニティAfgd2と前記ホストGHのアフィニティAfghの差が0.4eV以内である請求項9に記載の有機エレクトロルミネッセンス素子。
- 前記ホストBHが環式構造以外に二重結合を含まない化合物である請求項1乃至10のいずれかに記載の有機エレクトロルミネッセンス素子。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10785966.2A EP2442379B1 (en) | 2009-06-12 | 2010-06-10 | Organic electroluminescent element |
CN2010800226192A CN102439749A (zh) | 2009-06-12 | 2010-06-10 | 有机电致发光元件 |
JP2011518314A JP5231640B2 (ja) | 2009-06-12 | 2010-06-10 | 有機エレクトロルミネッセンス素子 |
EP16178014.3A EP3104428B1 (en) | 2009-06-12 | 2010-06-10 | Organic electroluminescence device |
KR1020117029524A KR101358478B1 (ko) | 2009-06-12 | 2010-06-10 | 유기 전계 발광 소자 |
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EP (2) | EP2442379B1 (ja) |
JP (1) | JP5231640B2 (ja) |
KR (1) | KR101358478B1 (ja) |
CN (1) | CN102439749A (ja) |
TW (1) | TW201106780A (ja) |
WO (1) | WO2010143434A1 (ja) |
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JPWO2010143434A1 (ja) | 2012-11-22 |
TW201106780A (en) | 2011-02-16 |
JP5231640B2 (ja) | 2013-07-10 |
EP2442379A4 (en) | 2014-03-05 |
KR101358478B1 (ko) | 2014-02-05 |
EP3104428B1 (en) | 2020-03-25 |
EP2442379A1 (en) | 2012-04-18 |
EP2442379B1 (en) | 2016-08-17 |
CN102439749A (zh) | 2012-05-02 |
KR20120034646A (ko) | 2012-04-12 |
EP3104428A1 (en) | 2016-12-14 |
US20100314644A1 (en) | 2010-12-16 |
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