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WO2014050093A1 - Matériau destiné à un élément électroluminescent organique, et élément électroluminescent organique produit en utilisant celui-ci - Google Patents

Matériau destiné à un élément électroluminescent organique, et élément électroluminescent organique produit en utilisant celui-ci Download PDF

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WO2014050093A1
WO2014050093A1 PCT/JP2013/005674 JP2013005674W WO2014050093A1 WO 2014050093 A1 WO2014050093 A1 WO 2014050093A1 JP 2013005674 W JP2013005674 W JP 2013005674W WO 2014050093 A1 WO2014050093 A1 WO 2014050093A1
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伸浩 藪ノ内
西村　和樹
栄田　暢
由美子 水木
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Idemitsu Kosan Co Ltd
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Definitions

  • the present invention relates to a material for an organic electroluminescence element and an organic electroluminescence element using the same.
  • an organic electroluminescence element (hereinafter also referred to as an organic EL element)
  • holes from the anode and electrons from the cathode are injected into the light emitting layer.
  • the injected holes and electrons are recombined to form excitons.
  • singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
  • the fluorescence type uses light emitted from singlet excitons, and therefore the internal quantum efficiency of the organic EL element is said to be limited to 25%.
  • the phosphorescent type since light emission by triplet excitons is used, it is known that the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.
  • the energy gap of the compound used in the light emitting layer must be large. This is because the value of the singlet energy of a compound (the energy difference between the lowest excited singlet state and the ground state) is usually the triplet energy of the compound (the energy between the lowest excited triplet state and the ground state). This is because it is larger than the value of the difference. Therefore, in order to efficiently confine the triplet energy of the phosphorescent dopant material in the device, first, a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must be used for the light emitting layer. I must.
  • hydrocarbon compounds with high oxidation resistance and reduction resistance which are useful in fluorescent elements, have a large energy gap due to a large spread of ⁇ electron clouds. Therefore, in a phosphorescent organic EL element, it is difficult to select such a hydrocarbon compound, and an organic compound containing a heteroatom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element. Furthermore, the fact that the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance.
  • an indolocarbazole derivative which has been conventionally known as a main skeleton of a hole transporting material and exhibits high triplet energy, has been used as a useful phosphorescent host material.
  • Patent Document 1 describes that a compound containing an indolocarbazole skeleton and a nitrogen-containing heterocyclic group in the same molecule is used as a material for an organic EL device.
  • This compound has a molecular design that balances charge transport by introducing an electron-deficient nitrogen-containing heterocyclic group into the hole-transporting indolocarbazole skeleton.
  • further improvement of the lifetime of the organic EL element is required, and development of a material for an organic EL element that can realize a longer lifetime is desired.
  • An object of the present invention is to provide an organic EL element capable of obtaining long-lived phosphorescence and a material for an organic EL element that realizes the organic EL element.
  • a material for an organic electroluminescence device represented by any one of the following formulas (1) to (6).
  • a 1 , A 2 , B 1 , B 2 and C are each independently a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom.
  • Y 1 to Y 10 each independently represent N (nitrogen atom) or CR a (C is a carbon atom).
  • R a independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted group;
  • the plurality of R a may be the same as or different from each other.
  • sa and ta each independently represent an integer of 0 to 5
  • sb and tb each represents an integer of 0 to 4
  • u represents an integer of 0 to 2
  • sa + sb + ta + tb + u is an integer of 1 to 5 . If sa is 1 ⁇ 5, A 1 and (Q 1) Q 1 of sa is bound.
  • sb is 1 to 4
  • at least one of Y 1 to Y 4 is bonded to B 1 of (B 1 -Q 1 ) sb .
  • ta is 1 ⁇ 5, Q 2 and A 2 (Q 2) ta is attached.
  • tb When tb is 1 to 4, at least one of Y 5 to Y 8 is bonded to B 2 of (B 2 -Q 2 ) tb .
  • u When u is 1 to 2, at least one of Y 9 and Y 10 is bonded to C of (CQ 3 ) u .
  • Q 1 , Q 2 and Q 3 each independently represents -Az-W q .
  • q represents an integer of 1 to 4. If Q 1 is are multiple, multiple Q 1 is may be the same or different from each other. If Q 2 there is a plurality, the plurality of Q 2 is may be the same or different from each other. If Q 3 is plural, Q 3 are may be the same or different from each other.
  • Az is a (q + 1) -valent group of a ring represented by the following formula (X).
  • Z 1 to Z 5 each independently represents a nitrogen atom or CR b .
  • R b are as defined above R a.
  • a part of R b in adjacent CR b may be bonded to form a ring structure.
  • the plurality of Az may be the same as or different from each other.
  • W represents a substituent X, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X, or a heterocyclic group having 5 to 30 ring atoms substituted with the substituent X.
  • the aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X and the heterocyclic group having 5 to 30 ring atoms substituted with the substituent X are substituents other than the substituent X. You may have.
  • the substituent X is an electron withdrawing group.
  • the plurality of Ws may be the same as or different from each other. ] 2.
  • a material for an organic electroluminescence device represented by any one of the following formulas (1) to (6).
  • a 1 , A 2 , B 1 , B 2 and C are each independently a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom.
  • Y 1 to Y 10 each independently represent N (nitrogen atom) or CR a (C is a carbon atom). However, when two adjacent Y 1 to Y 10 are CR a , a part of R a in adjacent CR a may be bonded to form a ring structure.
  • Each R a independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted group;
  • the plurality of R a may be the same as or different from each other.
  • sa and ta each independently represent an integer of 0 to 5
  • sb and tb each represents an integer of 0 to 4
  • u represents an integer of 0 to 2
  • sa + sb + ta + tb + u is an integer of 1 to 5 . If sa is 1 ⁇ 5, A 1 and (Q 1) Q 1 of sa is bound.
  • sb is 1 to 4
  • at least one of Y 1 to Y 4 is bonded to B 1 of (B 1 -Q 1 ) sb .
  • ta is 1 ⁇ 5, Q 2 and A 2 (Q 2) ta is attached.
  • tb When tb is 1 to 4, at least one of Y 5 to Y 8 is bonded to B 2 of (B 2 -Q 2 ) tb .
  • u When u is 1 to 2, at least one of Y 9 and Y 10 is bonded to C of (CQ 3 ) u .
  • Q 1 , Q 2 and Q 3 each independently represents -Az-W q .
  • q represents an integer of 1 to 4. If Q 1 is are multiple, multiple Q 1 is may be the same or different from each other. If Q 2 there is a plurality, the plurality of Q 2 is may be the same or different from each other. If Q 3 is plural, Q 3 are may be the same or different from each other.
  • Az is a (q + 1) -valent group of a ring represented by the following formula (X).
  • Z 1 to Z 5 each independently represents a nitrogen atom or CR b .
  • R b are as defined above R a.
  • a part of R b in adjacent CR b may be bonded to form a ring structure.
  • the plurality of Az may be the same as or different from each other.
  • W represents a substituent X, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X, or a heterocyclic group having 5 to 30 ring atoms substituted with the substituent X.
  • the aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X and the heterocyclic group having 5 to 30 ring atoms substituted with the substituent X are substituents other than the substituent X. You may have.
  • the substituent X is a group whose Hammett's rule constant ( ⁇ p (para)) takes a positive value. When there are a plurality of Ws, the plurality of Ws may be the same as or different from each other. ] 3.
  • a material for an organic electroluminescence device represented by any one of the following formulas (1) to (6).
  • a 1 , A 2 , B 1 , B 2 and C are each independently a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom.
  • Y 1 to Y 10 each independently represent N (nitrogen atom) or CR a (C is a carbon atom). However, when two adjacent Y 1 to Y 10 are CR a , a part of R a in adjacent CR a may be bonded to form a ring structure.
  • Each R a independently represents a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted group;
  • the plurality of R a may be the same as or different from each other.
  • sa and ta each independently represent an integer of 0 to 5
  • sb and tb each represents an integer of 0 to 4
  • u represents an integer of 0 to 2
  • sa + sb + ta + tb + u is an integer of 1 to 5 . If sa is 1 ⁇ 5, A 1 and (Q 1) Q 1 of sa is bound.
  • sb is 1 to 4
  • at least one of Y 1 to Y 4 is bonded to B 1 of (B 1 -Q 1 ) sb .
  • ta is 1 ⁇ 5, Q 2 and A 2 (Q 2) ta is attached.
  • tb When tb is 1 to 4, at least one of Y 5 to Y 8 is bonded to B 2 of (B 2 -Q 2 ) tb .
  • u When u is 1 to 2, at least one of Y 9 and Y 10 is bonded to C of (CQ 3 ) u .
  • Q 1 , Q 2 and Q 3 each independently represents -Az-W q .
  • q represents an integer of 1 to 4. If Q 1 is are multiple, multiple Q 1 is may be the same or different from each other. If Q 2 there is a plurality, the plurality of Q 2 is may be the same or different from each other. If Q 3 is plural, Q 3 are may be the same or different from each other.
  • Az is a (q + 1) -valent group of a ring represented by the following formula (X).
  • Z 1 to Z 5 each independently represents a nitrogen atom or CR b .
  • R b are as defined above R a.
  • a part of R b in adjacent CR b may be bonded to form a ring structure.
  • the plurality of Az may be the same as or different from each other.
  • W represents a substituent X, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X, or a heterocyclic group having 5 to 30 ring atoms substituted with the substituent X.
  • the aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X and the heterocyclic group having 5 to 30 ring atoms substituted with the substituent X are substituents other than the substituent X. You may have.
  • the substituent X is an electron withdrawing group in which the Hammett's rule substituent constant ( ⁇ p (para)) takes a positive value.
  • the plurality of Ws may be the same as or different from each other. ] 4). 4.
  • Az is a condensed polycyclic group containing a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 to 3 nitrogen atoms or a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 to 3 nitrogen atoms. 5.
  • Az is a condensed polycyclic group containing a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 or 2 nitrogen atoms, or a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 or 2 nitrogen atoms 6.
  • Az is a ring group selected from the group consisting of a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinazoline ring, and a substituted or unsubstituted quinoline ring. 6.
  • the sa is 1, the ta is 0, and the A 2 is a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms or a substituted or unsubstituted ring forming atom number of 5 to
  • the substituent X is selected from the group consisting of —CN, —F, —Cl, —Br, —I, —CO 2 R C , —COR C , —CF 3 , —SO 2 R C , —NO 2.
  • the material for an organic electroluminescent element according to any one of 1 to 11.
  • R C each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted group. Alternatively, it represents an unsubstituted alkyl group having 1 to 30 carbon atoms.
  • Electroluminescent element material R C each independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted group. Alternatively, it represents an unsubstituted alkyl group having 1 to 30 carbon atoms.) 16. 16.
  • W is a CN-substituted phenyl group, a CN-substituted biphenyl group, a CN-substituted naphthyl group, a CN-substituted diphenylfluorenyl group, a CN-substituted spirobifluorenyl group, a CN-substituted dimethylfluorenyl group, a CN-substituted phenanthrenyl group, CN 18.
  • the material for an organic electroluminescence device according to any one of 1 to 17, which is a substituted triphenylenyl group, a CN-substituted dibenzofuranyl group, or a CN-substituted dibenzothiophenyl group.
  • An organic film comprising one or more organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers contains the material for an organic electroluminescence device according to any one of 1 to 18 Electroluminescence element.
  • 20. 20. The organic electroluminescence device according to 19, wherein the light emitting layer contains the material for an organic electroluminescence device. 21. 21.
  • an organic EL device capable of obtaining long-lived phosphorescence and a material for an organic electroluminescence device for realizing the organic EL device.
  • FIG. 1 is a schematic sectional view showing an example of the organic EL device of the present invention.
  • the organic EL device material of the present invention is a compound represented by any one of the following formulas (1) to (6).
  • the above compound is a compound containing an indolocarbazole skeleton and a nitrogen-containing heterocyclic group (Az group possessed by Q 1 to Q 3 described later) in the same molecule, and the nitrogen-containing heterocyclic group is an electron-withdrawing group or / and Hammett.
  • Substituent X is a group having a positive substituent constant ( ⁇ p (para)), substituted with an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with substituent X, or substituent X And a heterocyclic group (W) having 5 to 30 ring atoms as a substituent.
  • the nitrogen-containing heterocyclic group has the substituent X or the substituent having the substituent X
  • the singlet energy (S1) of the compound is reduced and the structure is stabilized. As a result, the lifetime of the organic EL device using this compound is improved.
  • a 1 , A 2 , B 1 , B 2 and C are each independently a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Y 1 to Y 10 each independently represent N (nitrogen atom) or CR a (C is a carbon atom). However, when two adjacent Y 1 to Y 10 are CR a , a part of R a in adjacent CR a may be bonded to form a ring structure.
  • Each R a is independently a hydrogen atom, a halogen atom, a trifluoromethyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted silyl group, substituted or unsubstituted dialkylamino group having 2 to 20 carbon atoms Group, substituted or unsubstituted diarylamino group having 12 to 30 carbon atoms, substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms, substituted or unsubstituted ring atom having 5 to 30 ring atoms Represents a heterocycl
  • sa and ta each independently represents an integer of 0 to 5
  • sb and tb each independently represents an integer of 0 to 4
  • u represents an integer of 0 to 2
  • sa + sb + ta + tb + u represents 1 to 5 It is an integer. If sa is 1 ⁇ 5, A 1 and (Q 1) Q 1 of sa is bound. When sb is 1 to 4, at least one of Y 1 to Y 4 is bonded to B 1 of (B 1 -Q 1 ) sb . If ta is 1 ⁇ 5, Q 2 and A 2 (Q 2) ta is attached.
  • Q 1 , Q 2 and Q 3 are each independently a group represented by -Az-W q . q represents an integer of 1 to 4. If Q 1 is are multiple, multiple Q 1 is may be the same or different from each other. If Q 2 there is a plurality, the plurality of Q 2 is may be the same or different from each other. If Q 3 is plural, Q 3 are may be the same or different from each other.
  • Az is a (q + 1) -valent group of a ring represented by the following formula (X).
  • Z 1 to Z 5 each independently represent a nitrogen atom or CR b .
  • R b represents the same group as R a described above. However, when two adjacent Z 1 to Z 5 are CR b , a part of R b in adjacent CR b may be bonded to form a ring structure. If the R b there are a plurality, a plurality of R b may be the same or different from each other. When there are a plurality of Az, the plurality of Az may be the same as or different from each other.
  • Az includes (q + 1) -valent groups of isoquinoline ring, quinoxaline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, quinazoline ring, quinoline ring and acridine ring. These rings may be substituted or unsubstituted.
  • Az is a condensed polycyclic group containing a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 to 3 nitrogen atoms or a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 to 3 nitrogen atoms. preferable.
  • Az is a condensed polycyclic group containing a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 or 2 nitrogen atoms, or a substituted or unsubstituted nitrogen-containing 6-membered ring having 1 or 2 nitrogen atoms. Is preferred.
  • Az is a ring group selected from the group consisting of a substituted or unsubstituted pyrimidine ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinazoline ring, and a substituted or unsubstituted quinoline ring.
  • a ring group selected from a substituted or unsubstituted pyrimidine ring and a substituted or unsubstituted pyridine ring is preferable.
  • R represents a substituent, said R a, the same meanings as those mentioned R b.
  • R is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted
  • p represents an integer of 1 to 5.
  • W represents a substituent X, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X, or a heterocyclic group having 5 to 30 ring atoms substituted with the substituent X.
  • the aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with the substituent X and the heterocyclic group having 5 to 30 ring atoms substituted with the substituent X are substituents other than the substituent X. You may have.
  • the substituent X is an electron withdrawing group.
  • the substituent X is an electron-withdrawing group, a group having a positive Hammett's rule constant ( ⁇ p (para)), or a positive Hammett's substituent constant ( ⁇ p (para)).
  • the plurality of Ws may be the same as or different from each other.
  • the electron-withdrawing group is also called an electron-accepting group, and means an atomic group that attracts electrons from a substituted atomic group by an inductive effect or a resonance effect in the electronic theory.
  • the electron withdrawing group include those having a positive Hammett's substituent constant ( ⁇ p (para)).
  • ⁇ p Hammett's substituent constant
  • the electron barrier is increased in the hole transport layer adjacent to the light emitting layer, so that electrons are confined, and the electron in the hole injection / transport layer is By reducing the deterioration, the lifetime of the organic EL element can be improved.
  • R C independently represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted Represents an unsubstituted alkyl group having 1 to 30 carbon atoms.
  • the Hammett's rule substituent constant ( ⁇ p (para)) is a value described in Iwanami Rikagaku Dictionary 5th edition, P1063, Hitomi Suzuki, Organic Chemistry Course 2, Organic Reaction II Aromatic Compound, P119, and the like.
  • Preferred substituents X are —CN, —F, —CF 3 , —CO 2 R C , because of the chemical stability of the substituent (hard to decompose) and electrical stability (hard to generate radicals).
  • —COR C , —SO 2 R C may be mentioned.
  • the substituent X is —F, the triplet energy (T1) of the compound can be maintained high. Therefore, when the material of the present invention is used as the host of the light emitting layer, the efficiency of the organic EL device can be maintained or improved.
  • the substituent X is —CN
  • the singlet energy (S1) of the compound can be reduced not only by the inductive effect but also by the resonance effect. Therefore, when the material of the present invention is used as the host of the light emitting layer, the photochemical stability As a result, the lifetime of the organic EL element can be extended.
  • CN-substituted phenyl group CN-substituted biphenyl group, CN-substituted naphthyl group, CN-substituted diphenylfluorenyl group, CN-substituted spirobifluorenyl group, CN-substituted dimethylfluorenyl group, CN Examples thereof include a substituted phenanthrenyl group, a CN-substituted triphenylenyl group, a CN-substituted dibenzofuranyl group, and a CN-substituted dibenzothiophenyl group.
  • a 1 , A 2 , Y 1 to Y 10 , Q 1 and Q 2 each represent a group similar to the above formulas (1) to (6).
  • sa and ta each independently represents an integer of 0 to 5
  • sa + ta is an integer of 1 to 5.
  • the structure is stabilized by the interaction between N of indolocarbazole and Az of Q 1 and Q 2. Life expectancy can be expected. In addition, since the synthesis is simple, a high-purity material can be obtained, which is advantageous for extending the life of the light-emitting element.
  • the energy difference ( ⁇ ST) between S1 and T1 of the compound is reduced, the carrier injectability of the light emitting element is improved, the voltage is lowered, and the lifetime can be expected to be extended.
  • sa is 1
  • ta is 0, and
  • a 2 is a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 30 ring carbon atoms or a substituted or unsubstituted ring atom number of 5 to 30
  • the compound which is the heterocyclic group of is preferable.
  • the triplet energy (T1) of the compound is large, which is advantageous for increasing the efficiency of the organic EL device.
  • the energy difference ( ⁇ ST) between S1 and T1 of the compound is reduced, the carrier injectability of the organic EL element is improved, the voltage is lowered, and the lifetime can be expected to be extended. Furthermore, since the structure is stabilized by the interaction between N of indolocarbazole and Az of Q 1 , the lifetime of the organic EL element can be expected to be extended. Further, since the synthesis is simplified, a high-purity material can be obtained, which is advantageous for extending the life of the organic EL element. Further, as A 2, aromatic hydrocarbon ring groups, selecting a heterocyclic group, more structural stable, which is advantageous to the long life of the organic EL element. Further, sa is 1, Compound A 1 is a single bond.
  • alkyl group having 1 to 20 carbon atoms or 1 to 30 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and s-butyl.
  • halogen atom examples include fluorine, chlorine, bromine and iodine, and fluorine is preferable.
  • alkoxy group having 1 to 20 carbon atoms examples include methoxy group, ethoxy group, propoxy group, pentyloxy group, hexyloxy group and the like.
  • An alkoxy group having 1 to 5 carbon atoms is preferable.
  • haloalkyl group having 1 to 20 carbon atoms examples include those in which one or more hydrogen atoms are substituted with halogen atoms in the above alkyl group.
  • halogen atom fluorine is preferred.
  • examples thereof include a trifluoromethyl group and a 2,2-trifluoroethyl group.
  • it is a haloalkyl group having 1 to 5 carbon atoms.
  • haloalkoxy group having 1 to 20 carbon atoms examples include those obtained by substituting one or more hydrogen atoms with halogen atoms in the above alkoxy group.
  • halogen atom fluorine is preferred.
  • a haloalkoxy group having 1 to 5 carbon atoms is preferred.
  • Examples of the substituted or unsubstituted silyl group include a silyl group having 1 or more substituted or unsubstituted alkyl having 1 to 10 carbon atoms (alkylsilyl group), 1 substituted or unsubstituted aryl having 6 to 30 carbon atoms. Examples thereof include a silyl group (arylsilyl group) having the above or a silyl group having both an alkyl group and an aryl group.
  • trimethylsilyl group triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutyl
  • Examples include silyl group, dimethyl tertiary butyl silyl group, diethyl isopropyl silyl group, phenyl dimethyl silyl group, diphenyl methyl silyl group, diphenyl tertiary butyl silyl group, triphenyl silyl group, and the like.
  • Trimethyl silyl group, triethyl silyl group, t- A butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group are preferred.
  • dialkylamino group having 2 to 20 carbon atoms examples include dimethylamino group, diethylamino group, di-n-propylamino group, diisopropylamino group, di-n-butylamino group, di-s-butylamino group, diisobutylamino group , Di-t-butylamino group, dicyclopentylamino group, dicyclohexylamino group and the like.
  • diarylamino group having 12 to 30 carbon atoms examples include diphenylamino group, dinaphthylamino group, dibiphenylamino group, difluorenylamino group, phenylnaphthylamino group, phenylbiphenylamino group, phenylfluorenylamino group, and biphenyl.
  • Examples include a fluorenylamino group.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms include non-condensed aromatic hydrocarbon groups and condensed aromatic hydrocarbon groups. Specifically, in the case of a monovalent group, phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, spirofluorenyl group Group, 9,9-diphenylfluorenyl group, 9,9′-spirobi [9H-fluoren] -2-yl group, 9,9-dimethylfluorenyl group, benzo [c] phenanthrenyl group, benzo [a] Examples include triphenylenyl group, naphtho [1,2-c] phenanthrenyl group, naphtho [1,2-a] triphenylenyl
  • heterocyclic group having 5 to 30 ring atoms examples include non-fused heterocyclic groups and fused heterocyclic groups. More specifically, pyrrole ring, isoindole ring, benzofuran ring, isobenzofuran ring, dibenzothiophene ring, isoquinoline ring, quinoxaline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, Triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole
  • the optional substituent in the case of “substituted or unsubstituted” includes a halogen atom (fluorine, chlorine, bromine, iodine), a cyano group, an alkyl group having 1 to 20 carbon atoms (preferably 1 to 6), and 3 carbon atoms.
  • a cycloalkyl group having 20 to 20 (preferably 5 to 12), an alkoxy group having 1 to 20 carbon atoms (preferably 1 to 5), a haloalkyl group having 1 to 20 carbon atoms (preferably 1 to 5), and 1 to A haloalkoxy group having 20 (preferably 1 to 5), an alkylsilyl group having 1 to 10 carbon atoms (preferably 1 to 5), and an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 18) (aromatic Hydrocarbon groups), aryloxy groups having 6 to 30 (preferably 6 to 18) ring-forming carbon atoms, arylsilyl groups having 6 to 30 (preferably 6 to 18) carbon atoms, and 7 to 30 carbon atoms (preferably 7).
  • Examples of the optional substituent include an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, a substituted silyl group, an aromatic hydrocarbon group, and a heterocyclic group as described above.
  • Examples of the aryloxy group include those in which one hydrogen atom of a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group is substituted with an —O— group.
  • Examples of the aralkyl group include those in which one hydrogen atom of a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group is substituted with an alkyl group.
  • a fluorine atom, a cyano group, an alkyl group, a cycloalkyl group, an alkylsilyl group, an aryl group (aromatic hydrocarbon group), and a heteroaryl group (heterocyclic group) are particularly preferable.
  • carbon number ab in the expression “XX group having a substituted or unsubstituted carbon number ab” represents the number of carbons when the XX group is unsubstituted.
  • the number of carbon atoms of the substituent when the XX group is substituted is not included.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium (tritium).
  • the organic EL device of the present invention has an organic thin film layer containing a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers contains the above-described organic EL device material of the present invention.
  • the life of the organic EL element can be extended.
  • the organic thin film layer containing the organic EL device material of the present invention include a hole transport layer, a light emitting layer, an electron transport layer, a space layer, and a barrier layer, but are not limited thereto. Absent.
  • the material for an organic EL device of the present invention is preferably contained in the light emitting layer, and particularly preferably used as a host material for the light emitting layer. Further, the light emitting layer preferably contains a fluorescent light emitting material or a phosphorescent light emitting material, and particularly preferably contains a phosphorescent light emitting material. Furthermore, the organic EL device material of the present invention is also suitable as a barrier layer.
  • the organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit.
  • a tandem type having a plurality of light emitting units may be used, and among them, a phosphorescent type is preferable.
  • the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
  • typical element configurations of simple organic EL elements include the following element configurations.
  • Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided. A typical layer structure of the light emitting unit is shown below.
  • A Hole transport layer / light emitting layer (/ electron transport layer)
  • B Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
  • C Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
  • D Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • E Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
  • F Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
  • G Hole transport layer / electron barrier layer / light emitting layer (/ electron transport layer)
  • H Hole transport layer / light emitting layer / hole barrier layer (
  • Each phosphorescent or fluorescent light-emitting layer may have a different emission color.
  • hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / Examples include a layer configuration such as an electron transport layer.
  • An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer.
  • a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer.
  • the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
  • the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
  • a known material structure to be supplied can be used.
  • FIG. 1 shows a schematic configuration of an example of the organic EL element of the present invention.
  • the organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4.
  • the light emitting unit 10 includes a light emitting layer 5 including at least one phosphorescent light emitting layer including a phosphorescent host material and a phosphorescent dopant.
  • a hole injection / transport layer 6 or the like may be formed between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 or the like may be formed between the light emitting layer 5 and the cathode 4.
  • an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5.
  • a host combined with a fluorescent dopant is referred to as a fluorescent host
  • a host combined with a phosphorescent dopant is referred to as a phosphorescent host.
  • the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.
  • the organic EL element of the present invention is produced on a translucent substrate.
  • the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to use a material having a work function of 4.5 eV or more.
  • Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
  • the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the cathode plays a role of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer, and is preferably formed of a material having a small work function.
  • the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, you may take out light emission from the cathode side as needed.
  • An organic layer having a light emitting function includes a host material and a dopant material.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
  • the light emitting layer employs, for example, a double host (also referred to as host / cohost) that adjusts the carrier balance in the light emitting layer by combining an electron transporting host and a hole transporting host.
  • the light emitting layer preferably contains a first host material and a second host material, and the first host material is preferably the organic EL device material of the present invention.
  • you may employ adopt the double dopant from which each dopant light-emits by putting in 2 or more types of dopant materials with a high quantum yield. Specifically, a mode in which yellow emission is realized by co-evaporating a host, a red dopant, and a green dopant to make the light emitting layer common is used.
  • the above light-emitting layer is a laminate in which a plurality of light-emitting layers are stacked, so that electrons and holes are accumulated at the light-emitting layer interface, and the recombination region is concentrated at the light-emitting layer interface to improve quantum efficiency. Can do.
  • the ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.
  • the light emitting layer can be formed by a known method such as a vapor deposition method, a spin coating method, or an LB method (Langmuir Broadgett method).
  • the light emitting layer can also be formed by thinning a solution obtained by dissolving a binder such as a resin and a material compound in a solvent by a spin coating method or the like.
  • the light emitting layer is preferably a molecular deposited film.
  • the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state.
  • the thin film (molecular accumulation film) formed by the LB method can be classified by the difference in the aggregation structure and the higher-order structure, and the functional difference resulting therefrom.
  • the dopant material is selected from known fluorescent dopants exhibiting fluorescent emission or phosphorescent dopants exhibiting phosphorescent emission.
  • the fluorescent dopant is selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, fluorene derivatives, boron complexes, perylene derivatives, oxadiazole derivatives, anthracene derivatives, chrysene derivatives, and the like.
  • a fluoranthene derivative, a pyrene derivative, and a boron complex are used.
  • the phosphorescent dopant (phosphorescent material) that forms the light emitting layer is a compound that can emit light from the triplet excited state, and is not particularly limited as long as it emits light from the triplet excited state, but Ir, Pt, Os, Au, Cu, An organometallic complex containing at least one metal selected from Re and Ru and a ligand is preferable.
  • the ligand preferably has an ortho metal bond.
  • a metal complex containing a metal atom selected from Ir, Os and Pt is preferred in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved, and an iridium complex, an osmium complex, or a platinum complex.
  • iridium complexes and platinum complexes are more preferable, and orthometalated iridium complexes are particularly preferable.
  • the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1 to 70% by mass, more preferably 1 to 30% by mass. If the phosphorescent dopant content is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration quenching can be avoided.
  • the phosphorescent host is a compound having a function of efficiently emitting the phosphorescent dopant by efficiently confining the triplet energy of the phosphorescent dopant in the light emitting layer.
  • the organic EL device material of the present invention is suitable as a phosphorescent host.
  • the light emitting layer may contain 1 type of organic EL element material of this invention, and may contain 2 or more types of organic EL element material of this invention.
  • the emission wavelength of the phosphorescent dopant material contained in the light emitting layer is not particularly limited.
  • at least one of the phosphorescent dopant materials contained in the light emitting layer preferably has a peak emission wavelength of 490 nm to 700 nm, and more preferably 490 nm to 650 nm.
  • a luminescent color of a light emitting layer red, yellow, and green are preferable, for example.
  • a compound other than the material for the organic EL device of the present invention can be appropriately selected as the phosphorescent host according to the purpose.
  • the organic EL device material of the present invention and other compounds may be used in combination as a phosphorescent host material in the same light emitting layer, and when there are a plurality of light emitting layers, the phosphorescent host of one of the light emitting layers.
  • the material for an organic EL device of the present invention may be used as a material, and a compound other than the material for an organic EL device of the present invention may be used as a phosphorescent host material for another light emitting layer.
  • the organic EL device material of the present invention can be used for organic layers other than the light emitting layer. In that case, a compound other than the organic EL device material of the present invention is used as the phosphorescent host of the light emitting layer. May be.
  • compounds other than the organic EL device material of the present invention and suitable as a phosphorescent host include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, Pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluorenylidene derivatives And metal complexes of heterocycl
  • the organic EL element material of the present invention is used as the first host material
  • the organic EL element material other than the organic EL element material of the present invention is used as the second host material.
  • a compound may be used.
  • the terms “first host material” and “second host material” mean that the plurality of host materials contained in the light emitting layer have different structures from each other. It is not specified by the material content. It does not specifically limit as said 2nd host material, It is a compound other than the organic EL element material of this invention, and the same thing as the above-mentioned compound as a compound suitable as a phosphorescent host is mentioned.
  • the second host material a compound having no cyano group is preferable.
  • the second host is preferably a carbazole derivative, arylamine derivative, fluorenone derivative, or aromatic tertiary amine compound.
  • the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and still more preferably 10 to 50 nm.
  • the thickness is 5 nm or more, it is easy to form a light emitting layer, and when the thickness is 50 nm or less, an increase in driving voltage can be avoided.
  • the organic EL device of the present invention preferably has an electron donating dopant in the interface region between the cathode and the light emitting unit. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant means a material containing a metal having a work function of 3.8 eV or less, and specific examples thereof include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earths. Examples thereof include at least one selected from metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like.
  • alkali metal examples include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like.
  • a function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
  • alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable.
  • rare earth metals examples include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • alkali metal compound examples include alkali oxides such as Li 2 O, Cs 2 O, and K 2 O, and alkali halides such as LiF, NaF, CsF, and KF, and LiF, Li 2 O, and NaF are preferable.
  • alkaline earth metal compound examples include BaO, SrO, CaO, and Ba x Sr 1-x O (0 ⁇ x ⁇ 1), Ba x Ca 1-x O (0 ⁇ x ⁇ 1) mixed with these. BaO, SrO, and CaO are preferable.
  • the rare earth metal compound, YbF 3, ScF 3, ScO 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the like, YbF 3, ScF 3, TbF 3 are preferable.
  • the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl thiadiazole, hydroxydiaryl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.
  • the electron donating dopant it is preferable to form a layered or island shape in the interface region.
  • a forming method while depositing an electron donating dopant by resistance heating vapor deposition, an organic compound (light emitting material or electron injecting material) that forms an interface region is simultaneously deposited, and the electron donating dopant is dispersed in the organic compound.
  • the electron donating dopant is formed in a layered form
  • the reducing dopant is vapor-deposited by a resistance heating vapor deposition method. .1 nm to 15 nm.
  • the electron donating dopant is formed in an island shape
  • the electron donating dopant is deposited by resistance heating vapor deposition alone, preferably The island is formed with a thickness of 0.05 nm to 1 nm.
  • the electron transport layer is an organic layer formed between the light emitting layer and the cathode, and has a function of transporting electrons from the cathode to the light emitting layer.
  • an organic layer close to the cathode may be defined as an electron injection layer.
  • the electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.
  • an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
  • the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
  • a nitrogen-containing ring metal chelate complex represented by the following formula (A) is preferable.
  • R 2 to R 7 in the formula (A) which is a nitrogen-containing ring metal chelate complex are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, An alkoxy group having 1 to 40 carbon atoms, an aryloxy group having 6 to 50 carbon atoms, an alkoxycarbonyl group, or an aromatic heterocyclic group having 5 to 50 ring carbon atoms, which may be substituted. .
  • Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.
  • the amino group which may be substituted include an alkylamino group, an arylamino group and an aralkylamino group.
  • the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 .
  • Q 1 and Q 2 each independently represents an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 1 to 20 carbon atoms.
  • One of Q 1 and Q 2 may be a hydrogen atom or a deuterium atom.
  • the arylamino group is represented as —NAr 1 Ar 2, and Ar 1 and Ar 2 each independently represent a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group having 6 to 50 carbon atoms.
  • Ar 1 and Ar 2 may be a hydrogen atom or a deuterium atom.
  • the hydrocarbon group having 1 to 40 carbon atoms includes an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and an aralkyl group.
  • the alkoxycarbonyl group is represented as —COOY ′, and Y ′ represents an alkyl group having 1 to 20 carbon atoms.
  • M is aluminum (Al), gallium (Ga) or indium (In), and is preferably In.
  • L is a group represented by the following formula (A ′) or (A ′′).
  • R 8 to R 12 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and the groups adjacent to each other are cyclic structures May be formed.
  • R 13 to R 27 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms.
  • An annular structure may be formed.
  • the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in the formula (A ′) and the formula (A ′′) is a nitrogen-containing ring metal chelate complex in the formula (A).
  • the divalent group in the case where the adjacent groups of R 8 to R 12 and R 13 to R 27 form a cyclic structure is the same as the hydrocarbon group represented by R 2 to R 7 of Examples include a methylene group, a pentamethylene group, a hexamethylene group, a diphenylmethane-2,2′-diyl group, a diphenylethane-3,3′-diyl group, and a diphenylpropane-4,4′-diyl group.
  • 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
  • a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used.
  • 8-quinolinol or 8-hydroxyquinoline a metal chelate oxinoid compound containing a chelate of oxine
  • tris (8-quinolinol) aluminum is used.
  • an oxadiazole derivative the following can be mentioned.
  • Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 each represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms
  • Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same or different.
  • the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
  • substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
  • Ar 20 , Ar 23 and Ar 24 each represent a substituted or unsubstituted divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms, and Ar 23 and Ar 24 are identical to each other. But it can be different.
  • the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
  • substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
  • electron transfer compounds those having good thin film forming properties are preferably used.
  • Specific examples of these electron transfer compounds include the following.
  • nitrogen-containing heterocyclic derivative as the electron transfer compound examples include nitrogen-containing compounds that are not metal complexes. Examples thereof include a 5-membered ring or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C).
  • X represents a carbon atom or a nitrogen atom.
  • Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
  • the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group containing a 5-membered ring and / or a 6-membered ring. Further, in the case of a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing aromatic polycyclic having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Ring organic compounds are preferred.
  • the nitrogen-containing heterocyclic ring of the nitrogen-containing heterocyclic derivative is selected from, for example, groups represented by the following formulae.
  • R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
  • preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula (D1). HAr-L 1 -Ar 1 -Ar 2 (D1)
  • HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms
  • L 1 is a single bond, substituted or unsubstituted aromatic hydrocarbon having 6 to 40 carbon atoms.
  • Ar 1 is a substituted or unsubstituted 2 to 6 carbon atom having 2 to 6 carbon atoms.
  • Ar 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, or a substituted or unsubstituted aromatic group having 3 to 40 carbon atoms. It is a heterocyclic group or a condensed aromatic heterocyclic group.
  • HAr is selected from the following group, for example.
  • L 1 in the formula (D1) is selected from the following group, for example.
  • Ar 1 in the formula (D1) is selected from, for example, arylanthranyl groups of the following formulas (D2) and (D3).
  • R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.
  • R 1 to R 8 may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom or a deuterium atom.
  • Ar 2 in the formula (D1) is selected from the following group, for example.
  • the following compounds are also preferably used for the nitrogen-containing heterocyclic derivative as the electron-transfer compound.
  • R 1 to R 4 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aliphatic group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 3 to 20
  • X 1 and X 2 are each independently Represents an oxygen atom, a sulfur atom, or a dicyanomethylene group.
  • the following compounds are also preferably used as the electron transfer compound.
  • R 1 , R 2 , R 3 and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula (D6). It is.
  • R 5 , R 6 , R 7 , R 8 and R 9 are the same or different from each other, and are a hydrogen atom, a deuterium atom, a saturated or unsaturated alkoxyl group having 1 to 20 carbon atoms.
  • At least one of R 5 , R 6 , R 7 , R 8 and R 9 is a group other than a hydrogen atom or a deuterium atom.
  • the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
  • the electron transport layer of the organic EL device of the present invention particularly preferably contains at least one nitrogen-containing heterocyclic derivative represented by the following formulas (E) to (G).
  • Z 1 , Z 2 and Z 3 are each independently a nitrogen atom or a carbon atom.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted carbon An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
  • n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R 1 may be the same or different from each other. Further, two adjacent R 1 may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • Ar 1 is 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.
  • Ar 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Alternatively, it is an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
  • Ar 1 or Ar 2 is a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted condensed aromatic group having 9 to 50 ring atoms. It is a heterocyclic group.
  • Ar 3 is 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 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent ring having 9 to 50 ring atoms.
  • aryl group having 6 to 50 ring carbon atoms examples include phenyl, naphthyl, anthryl, phenanthryl, naphthacenyl, chrysenyl, pyrenyl, biphenyl, terphenyl, tolyl, fluoranthenyl, fluorenyl Groups and the like.
  • heteroaryl groups having 5 to 50 ring atoms include pyrrolyl, furyl, thienyl, silolyl, pyridyl, quinolyl, isoquinolyl, benzofuryl, imidazolyl, pyrimidyl, carbazolyl, selenophenyl Group, oxadiazolyl group, triazolyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinoxalinyl group, acridinyl group, imidazo [1,2-a] pyridinyl group, imidazo [1,2-a] pyrimidinyl group and the like.
  • Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • Examples of the haloalkyl group having 1 to 20 carbon atoms include groups obtained by substituting one or more hydrogen atoms of the alkyl group with at least one halogen atom selected from fluorine, chlorine, iodine and bromine.
  • Examples of the alkoxy group having 1 to 20 carbon atoms include groups having the alkyl group as an alkyl moiety.
  • Examples of the arylene group having 6 to 50 ring carbon atoms include groups obtained by removing one hydrogen atom from the aryl group.
  • Examples of the divalent condensed aromatic heterocyclic group having 9 to 50 ring atoms include groups obtained by removing one hydrogen atom from the condensed aromatic heterocyclic group described as the heteroaryl group.
  • the thickness of the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm. Moreover, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative as a component of the electron injection layer that can be provided adjacent to the electron transport layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
  • an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
  • preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
  • preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe.
  • preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
  • preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
  • the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides.
  • the preferred thickness of the layer is about 0.1 nm to 15 nm.
  • the electron injection layer in the present invention is preferable even if it contains the above-mentioned electron donating dopant.
  • an organic layer close to the anode may be defined as a hole injection layer.
  • the hole injection layer has a function of efficiently injecting holes from the anode into the organic layer unit.
  • an aromatic amine compound for example, an aromatic amine derivative represented by the following formula (H) is preferably used.
  • Ar 1 ⁇ Ar 4 is a substituted or an aromatic hydrocarbon group or fused aromatic hydrocarbon group unsubstituted ring carbon atoms 6 to 50, a substituted or unsubstituted ring atoms of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups and aromatic heterocyclic groups or condensed aromatic heterocyclic groups are bonded.
  • L represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 50. Represents an aromatic heterocyclic group or a condensed aromatic heterocyclic group.
  • An aromatic amine represented by the following formula (J) is also preferably used for forming the hole transport layer.
  • the hole transport layer of the organic EL device of the present invention may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
  • the thickness of the hole transport layer is not particularly limited, but is preferably 10 to 200 nm.
  • a layer containing an acceptor material may be bonded to the anode side of the hole transport layer or the first hole transport layer. This is expected to reduce drive voltage and manufacturing costs.
  • the acceptor material a compound represented by the following formula (K) is preferable.
  • R 21 to R 26 may be the same as or different from each other, and each independently represents a cyano group, —CONH 2 , a carboxyl group, or —COOR 27 (R 27 is a group having 1 to 20 carbon atoms) Represents an alkyl group or a cycloalkyl group having 3 to 20 carbon atoms, provided that one or more pairs of R 21 and R 22 , R 23 and R 24 , and R 25 and R 26 are combined together.
  • a group represented by —CO—O—CO— may be formed.
  • R 27 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
  • the thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.
  • the carrier injection ability can be improved by doping the donor material (n) or acceptor material (p). Can be adjusted.
  • n doping is a method of doping a metal such as Li or Cs into an electron transport material
  • p doping is F 4 TCNQ (2, 3, 5, 6) as a hole transport material.
  • -Tetrafluor-7,7,8,8-tetracyanoquinodimethane and the like.
  • the space layer is a fluorescent layer for the purpose of adjusting the carrier balance so that excitons generated in the phosphorescent layer are not diffused into the fluorescent layer. It is a layer provided between the layer and the phosphorescent light emitting layer.
  • the space layer can be provided between the plurality of phosphorescent light emitting layers. Since the space layer is provided between the light emitting layers, a material having both electron transport properties and hole transport properties is preferable. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.
  • the organic EL device of the present invention preferably has a barrier layer such as an electron barrier layer, a hole barrier layer, or a triplet barrier layer in a portion adjacent to the light emitting layer.
  • the electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer
  • the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. is there.
  • the triplet barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the surrounding layers, and confins the triplet excitons in the light emitting layer, thereby transporting electrons other than the light emitting dopant of the triplet excitons. It has a function of suppressing energy deactivation on the molecules of the layer.
  • the phosphorescent devices When providing the triplet barrier layer, the phosphorescent devices, triplet energy E T d of the phosphorescent dopant in the light emitting layer and the triplet energy of the compound used as a triplet barrier layer and E T TB, E T d ⁇ If the energy magnitude relationship of E T TB is satisfied, the triplet exciton of the phosphorescent dopant is confined (cannot move to other molecules) and the energy deactivation path other than light emission on the dopant is interrupted. It is assumed that light can be emitted with high efficiency.
  • the organic EL element material of the present invention can be used as a triplet barrier layer having a TTF element structure described in International Publication WO2010 / 134350A1.
  • the electron mobility of the material constituting the triplet barrier layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm.
  • the electron mobility is determined by impedance spectroscopy.
  • the electron injection layer is desirably 10 ⁇ 6 cm 2 / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm. This facilitates the injection of electrons from the cathode into the electron transport layer, and also promotes the injection of electrons into the adjacent barrier layer and the light emitting layer, thereby enabling driving at a lower voltage.
  • Example 1 Manufacture of organic EL elements
  • a glass substrate with an ITO transparent electrode of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
  • the glass substrate with the transparent electrode line after washing is mounted on the substrate holder of the vacuum deposition apparatus, and the following electron-accepting (acceptor) compound is first formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed.
  • HI-1 was vapor-deposited to form a compound HI-1 film having a thickness of 5 nm.
  • the following aromatic amine derivative (compound HT-1) was deposited as a first hole transporting material to form a first hole transporting layer having a thickness of 40 nm.
  • the following aromatic amine derivative (Compound HT-2) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
  • the compound H-1 synthesized in Synthesis Example 1 as a host material and the following compound PQIr (acac) as a phosphorescent material are co-evaporated to form a phosphorescent layer having a film thickness of 40 nm.
  • the concentration of the compound PQIr (acac) in the light emitting layer was 8.0% by mass.
  • This co-deposited film functions as a light emitting layer.
  • the following compound ET-1 was formed to a thickness of 40 nm. This compound ET-1 film functions as an electron transport layer.
  • LiF was used as an electron injecting electrode (cathode) and the film thickness was set to 1 nm at a film forming rate of 0.1 angstrom / min.
  • Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
  • the obtained organic EL device was evaluated for 80% life (time until the luminance decreased to 80% of the initial light emission luminance) when driven at a constant current with an initial light emission luminance of 10,000 cd / m 2 .
  • the results are shown in Table 1.
  • Example 2 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that Compound H-2 synthesized in Synthesis Example 2 was used instead of Compound H-1 as the host material for the light emitting layer. The results are shown in Table 1.
  • Comparative Example 1 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the following compound F-1 was used instead of the compound H-1 as a host material for the light emitting layer. The results are shown in Table 1.
  • Example 3 An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the following compound Ir (tpiq) 2 (acac) was used in place of the compound PQIr (acac) as the phosphorescent material of the light emitting layer. The results are shown in Table 1.
  • Example 4 An organic EL device was prepared and evaluated in the same manner as in Example 3 except that Compound H-2 synthesized in Synthesis Example 2 was used instead of Compound H-1 as the host material for the light emitting layer. The results are shown in Table 1.
  • Comparative Example 2 An organic EL device was prepared and evaluated in the same manner as in Example 3 except that the compound F-1 was used instead of the compound H-1 as a host material for the light emitting layer. The results are shown in Table 1.
  • the organic EL device material of the present invention is useful as a material for realizing a long-life phosphorescent organic EL device.

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