WO2014097813A1 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- WO2014097813A1 WO2014097813A1 PCT/JP2013/081370 JP2013081370W WO2014097813A1 WO 2014097813 A1 WO2014097813 A1 WO 2014097813A1 JP 2013081370 W JP2013081370 W JP 2013081370W WO 2014097813 A1 WO2014097813 A1 WO 2014097813A1
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- aromatic heterocyclic
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- 0 *([n](cc1)c2c1*=CCC2)N1C(CCC=C2)=C2C#CC1 Chemical compound *([n](cc1)c2c1*=CCC2)N1C(CCC=C2)=C2C#CC1 0.000 description 4
- YUQNJHQBDOERSA-UHFFFAOYSA-N CC1C=C=CC=C1 Chemical compound CC1C=C=CC=C1 YUQNJHQBDOERSA-UHFFFAOYSA-N 0.000 description 2
- FYYYJNJWYVDKCP-UHFFFAOYSA-N CCc(cc1)ccc1-[n]1c(c2c(cc3)c(cccc4)c4[n]2-c2cc(-c4ccccc4)nc(-c4ccccc4)n2)c3c2c1cccc2 Chemical compound CCc(cc1)ccc1-[n]1c(c2c(cc3)c(cccc4)c4[n]2-c2cc(-c4ccccc4)nc(-c4ccccc4)n2)c3c2c1cccc2 FYYYJNJWYVDKCP-UHFFFAOYSA-N 0.000 description 1
- ZDEQEVRDHVHLOL-UHFFFAOYSA-N CCc(cc1)ccc1-c1nc(-c2ccc(CC)cc2)nc(CCC2c3ccccc3-c3ccc(c(cccc4)c4[n]4-c5ccccc5)c4c3C2)c1 Chemical compound CCc(cc1)ccc1-c1nc(-c2ccc(CC)cc2)nc(CCC2c3ccccc3-c3ccc(c(cccc4)c4[n]4-c5ccccc5)c4c3C2)c1 ZDEQEVRDHVHLOL-UHFFFAOYSA-N 0.000 description 1
- SDHNJSIZTIODFW-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c1ccc2[s]c(ccc(-[n]3c(cccc4)c4c4c3cccc4)c3)c3c2c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c1ccc2[s]c(ccc(-[n]3c(cccc4)c4c4c3cccc4)c3)c3c2c1 SDHNJSIZTIODFW-UHFFFAOYSA-N 0.000 description 1
- XUKCIYXHVMSRRS-UHFFFAOYSA-N c(cc1)ccc1-[n](c(cccc1)c1c1c2c3c4cccc3)c1ccc2[n]4-c1cccc(-c2ccc3[o]c(cccc4)c4c3c2)n1 Chemical compound c(cc1)ccc1-[n](c(cccc1)c1c1c2c3c4cccc3)c1ccc2[n]4-c1cccc(-c2ccc3[o]c(cccc4)c4c3c2)n1 XUKCIYXHVMSRRS-UHFFFAOYSA-N 0.000 description 1
- NYEATDNHOAYDIZ-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)cc(c2ccc(c(cccc3)c3[n]3-c4ccccc4)c3c22)c1[n]2-c1nc(-c2ccccc2)cc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)cc(c2ccc(c(cccc3)c3[n]3-c4ccccc4)c3c22)c1[n]2-c1nc(-c2ccccc2)cc(-c2ccccc2)n1 NYEATDNHOAYDIZ-UHFFFAOYSA-N 0.000 description 1
- WHUCJGIWJYFHAT-UHFFFAOYSA-N c(cc1)ccc1-c(cc1c2c3cccc2)c(c2ccccc2[n]2-c4nc(-c5ccccc5)cc(-c5ccccc5)n4)c2c1[n]3-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1c2c3cccc2)c(c2ccccc2[n]2-c4nc(-c5ccccc5)cc(-c5ccccc5)n4)c2c1[n]3-c1ccccc1 WHUCJGIWJYFHAT-UHFFFAOYSA-N 0.000 description 1
- DRDQYZXAHSSJPB-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c2ccccc2)nc(-[n]2c(c3c(cc4)c5ccccc5[n]3-c3ccccc3)c4c3ccccc23)n1 Chemical compound c(cc1)ccc1-c1cc(-c2ccccc2)nc(-[n]2c(c3c(cc4)c5ccccc5[n]3-c3ccccc3)c4c3ccccc23)n1 DRDQYZXAHSSJPB-UHFFFAOYSA-N 0.000 description 1
- FUVPICQBOARXBZ-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(-c2cc(-c3ccccc3)nc(-[n]3c(c4c(cc5)c(cccc6)c6[n]4-c4ccccc4)c5c4ccccc34)n2)c1 Chemical compound c(cc1)ccc1-c1cccc(-c2cc(-c3ccccc3)nc(-[n]3c(c4c(cc5)c(cccc6)c6[n]4-c4ccccc4)c5c4ccccc34)n2)c1 FUVPICQBOARXBZ-UHFFFAOYSA-N 0.000 description 1
- PRWZPYJFTYXDJB-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)cc(-c(cc2)cc3c2[o]c2ccccc32)n1 Chemical compound c(cc1)ccc1-c1nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)cc(-c(cc2)cc3c2[o]c2ccccc32)n1 PRWZPYJFTYXDJB-UHFFFAOYSA-N 0.000 description 1
- FOGIHRPCWOBEDE-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-[n]2c(cccc3)c3c3c2cccc3)nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1nc(-[n]2c(cccc3)c3c3c2cccc3)nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)c1 FOGIHRPCWOBEDE-UHFFFAOYSA-N 0.000 description 1
- IZHWUVWZQLLZPE-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-[n]2c3ccc(c4ccccc4[n]4-c5ccccc5)c4c3c3c2cccc3)nc(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1nc(-[n]2c3ccc(c4ccccc4[n]4-c5ccccc5)c4c3c3c2cccc3)nc(-c2ccccc2)c1 IZHWUVWZQLLZPE-UHFFFAOYSA-N 0.000 description 1
- WBYOVFFZHSOYNV-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)cc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c(cc2)cc(c3ccccc33)c2[n]3-c2ccccc2)cc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)n1 WBYOVFFZHSOYNV-UHFFFAOYSA-N 0.000 description 1
- BLSVUWFGCDBGHG-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2ccccc2)c1 BLSVUWFGCDBGHG-UHFFFAOYSA-N 0.000 description 1
- GMRHOUBJXAOXPH-UHFFFAOYSA-N c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-[n](c1c2cccc1)c(cc1)c2c(c2ccccc22)c1[n]2-c1nc(-[n]2c(cccc3)c3c3c2cccc3)ccc1 Chemical compound c(cc1)ccc1N(c1ccccc1)c(cc1)ccc1-[n](c1c2cccc1)c(cc1)c2c(c2ccccc22)c1[n]2-c1nc(-[n]2c(cccc3)c3c3c2cccc3)ccc1 GMRHOUBJXAOXPH-UHFFFAOYSA-N 0.000 description 1
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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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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Definitions
- the present invention relates to an organic electroluminescent device (hereinafter referred to as an organic EL device).
- an organic EL element has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. That is, in an organic EL device, when an electric field is applied to both electrodes, electrons are injected from the cathode, holes are injected from the anode, and light is emitted as energy when they are recombined in the light emitting layer. Is used.
- organic EL elements using organic thin films have been developed.
- developments have been made to increase luminous efficiency.
- the efficiency of carrier injection from the electrode was improved by optimizing the type of electrode.
- the development of devices using a hole transport layer made of aromatic diamine and a light-emitting layer / electron transport layer made of 8-hydroxyquinoline aluminum complex (hereinafter referred to as Alq3) has led to a significant improvement in luminous efficiency compared to conventional devices.
- Alq3 8-hydroxyquinoline aluminum complex
- Examples of the host material used for the light emitting layer of the organic EL element include carbazole compounds, oxazole compounds, and triazole compounds, but none of them are practically durable in terms of efficiency and lifetime.
- Patent Document 1 discloses an indolocarbazole compound, its use as a hole transport material is recommended, and there is no disclosure of its use as a mixed host material.
- Patent Document 2 discloses the use of an indolocarbazole compound as a host material, but does not teach the usefulness of the indolocarbazole compound as a mixed host material.
- Patent Documents 3 and 4 disclose the use of indolocarbazole compounds as a mixed host, but do not teach that useful effects are manifested in combination with specific carbazole compounds.
- Patent Documents 5, 6, and 7 disclose the use of indolocarbazole compounds and carbazole compounds as mixed hosts, but teach the useful effects of combinations of specific indolocarbazole compounds and specific carbazole compounds. It is not a thing.
- Patent Documents 8 and 9 disclose specific carbazole compounds, but do not teach useful effects of combinations with specific indolocarbazole compounds.
- An object of the present invention is to provide a practically useful organic EL element having high efficiency and high driving stability while being low in voltage in view of the above-described present situation.
- the present invention provides an organic electroluminescent device comprising one or more light emitting layers between an anode and a cathode facing each other, wherein at least one light emitting layer contains at least two host materials and at least one light emitting dopant,
- the at least two host materials include at least one host material selected from compounds represented by any one of the following general formulas (1) to (2) and at least selected from compounds represented by the following general formula (3):
- the present invention relates to an organic electroluminescent element including one host material.
- ring a, ring c, and ring c ′ each independently represent an aromatic ring or a heterocyclic ring represented by formula (a1) that is condensed at any position of two adjacent rings
- Ring b, Ring d, and Ring d ′ each independently represent a heterocyclic ring represented by Formula (b1) that is condensed at any position of two adjacent rings
- X 1 represents CR 7 or N
- Ar 1 and Ar 2 each independently represent an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms
- Z is an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or 2 to 10 linked aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group.
- R 1 to R 7 are each independently hydrogen, cyano group, alkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 38 carbon atoms, alkenyl group having 2 to 20 carbon atoms, or alkynyl group having 2 to 20 carbon atoms.
- each L 3 independently represents hydrogen or a monovalent group, and E represents oxygen or sulfur. Moreover, a part or all of hydrogen in general formula (1), (2) and general formula (3) may be substituted by deuterium.
- Ar 1 or Ar 2 is a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, and X 1 is CR 7 .
- At least one of L 3 in the general formula (3) is a monovalent group represented by the formula (e1).
- each L 4 independently represents hydrogen, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms.
- X 2 each independently represents CL 4 or nitrogen, and the plurality of L 4 may be the same or different,
- the aromatic hydrocarbon group or aromatic heterocyclic group in L 4 may have a
- the compound represented by the general formula (3) is preferably a compound represented by the general formula (4), and the compound represented by the general formula (4) is a compound represented by the general formula (5). It is preferable.
- the difference in electron affinity ( ⁇ EA) between the material selected from the compound represented by any one of the general formulas (1) to (2) and the material selected from the compound represented by the general formula (3) is 0.1 eV. It is desirable to be larger.
- the luminescent dopant is preferably an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
- the organic EL device of the present invention has a lowest excited triplet energy high enough to confine the lowest excited triplet energy of a phosphorescent molecule by using a specific compound as a mixed host, while being at a low voltage. Therefore, there is no outflow of energy from the light emitting layer, and high efficiency and long life can be achieved.
- the organic electroluminescent device of the present invention is an organic electroluminescent device including one or more light emitting layers between an anode and a cathode facing each other, wherein at least one light emitting layer contains at least two host materials and at least one light emitting dopant.
- One of the two host materials is a host material selected from the compounds represented by any one of the following general formulas (1) to (2), and the other one is represented by the following general formula ( It is a host material selected from the compounds represented by 3).
- ring a, ring c, and ring c ′ each independently represent an aromatic ring or a heterocyclic ring represented by formula (a1) that is condensed at any position of two adjacent rings.
- Ring b, ring d, and ring d ′ each independently represent a heterocyclic ring represented by the formula (b1) that is condensed at an arbitrary position of two adjacent rings.
- X 1 represents CR 7 or N, preferably CR 7 .
- the aromatic hydrocarbon ring or heterocyclic ring represented by the formula (a1) can be condensed with two adjacent rings at any position. There are positions that cannot be structurally condensed.
- the aromatic hydrocarbon ring or heterocyclic ring represented by the formula (a1) has six sides, but is not condensed with two adjacent rings at two adjacent sides.
- the heterocyclic ring represented by the formula (b1) can be condensed with two adjacent rings at any position, but there are positions where it cannot be structurally condensed.
- the heterocyclic ring represented by the formula (b1) has five sides, but does not condense with two adjacent rings at two adjacent sides, and also condenses with an adjacent ring at a side including a nitrogen atom. None do. Therefore, the types of isomers of the compounds represented by the general formulas (1) and (2) are limited.
- Ar 1 to Ar 2 represent an aromatic hydrocarbon group having 6 to 22 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 6 carbon atoms, Each of the aromatic hydrocarbon group or the aromatic heterocyclic group may have a substituent.
- the general formula (1) or the general formula (2) is understood to include the formula (a1) and the formula (b1).
- Ar 1 to Ar 2 are preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 5 carbon atoms, and the monocyclic aromatic heterocyclic group is a 6-membered ring It is preferable that Ar 1 is a p + 1 valent group, and Ar 2 is a q + 1 valent group.
- Ar 1 to Ar 2 include benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, tridene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, Pyrene, chrysene, tetraphen, tetraphen, tetracene, pleiaden, picene, perylene, pentaphen, pentacene, tetraphenylene, cholantolylene, helicene, hexaphen, rubicene, coronene, trinaphthylene, heptaphene, pyranthrene, furan, thiophene, pyrrole, pyrazole, Tellurazole, selenazole,
- Z represents an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or an aromatic ring of the aromatic hydrocarbon group and the aromatic heterocyclic group.
- the linking group is an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a divalent linked aromatic group formed by linking 2 to 7 thereof
- the linking group is an aromatic hydrocarbon group having 6 to 18 carbon atoms or a monocyclic aromatic heterocyclic group having 3 to 5 carbon atoms, and the monocyclic aromatic heterocyclic group is preferably a 6-membered ring.
- Each aromatic ring may independently have a substituent.
- Z are the same as those described for the aromatic hydrocarbon group, aromatic heterocyclic group or linked aromatic group in L 1 and L 2 , but the aromatic heterocyclic group bonded to N has 3 carbon atoms. 6 to 6 monocyclic aromatic heterocyclic groups.
- L 1 and L 2 are each an aromatic hydrocarbon group having 6 to 22 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or 2 to 10 A linked aromatic group formed by linking these groups is shown, and each of these groups may have a substituent.
- An aromatic hydrocarbon group having 6 to 18 carbon atoms, an aromatic heterocyclic group having 3 to 16 carbon atoms, or a linked aromatic group formed by connecting 2 to 7 carbon atoms is preferable.
- L 1 and L 2 include benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, tridene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, Pyrene, chrysene, tetraphen, tetracene, pleiaden, picene, perylene, pentaphen, pentacene, tetraphenylene, cholanthrylene, helicene, hexaphene, rubicene, coronene, trinaphthylene, heptaphene, pyranthrene, furan, benzofuran, isobenzofuran, xanthene, oxatolene, Dibenzofuran, per
- examples of the linked aromatic group in L 1 and L 2 include linkage modes as shown in formulas (7) to (9).
- Examples of the linked aromatic group in Z include linkage modes such as those represented by formulas (10) to (12).
- Ar 4 to Ar 29 represent a substituted or unsubstituted aromatic ring.
- the aromatic ring means a ring of an aromatic hydrocarbon compound or an aromatic heterocyclic compound, and means a monovalent or higher group. When the aromatic ring is a substituted aromatic ring, the substituent is not an aromatic ring.
- Ar 17 , Ar 20 , Ar 22 , Ar 24 , Ar 26 are groups bonded to N.
- L 1 , L 2 and R 1 to R 7 each represents an integer of 0 to 7, preferably 0 to 5, and more preferably 0 to 3.
- h, i, j, k, l, and m represent an integer of 4, and n represents an integer of 2.
- aromatic hydrocarbon group or aromatic heterocyclic group in Ar 1 , Ar 2 , L 1 , L 2 , Z, and R 1 to R 7 may have a substituent or a substituent.
- substituents include cyano, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl , Phenylmethyl, phenylethyl, phenylicosyl, naphthylmethyl, anthranylmethyl, phenanthrenylmethyl, pyrenylmethyl, vinyl, propenyl, butenyl, pentenyl, decenyl, icocenyl, ethynyl, propargyl, butynyl, pentynyl, decynyl, icosinyl
- C1-12 alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, phenylmethyl, phenylethyl, naphthylmethyl, anthranylmethyl, phenanthrenylmethyl, pyrenylmethyl C7-20 aralkyl groups such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonyloxy, deoxy, etc., C1-10 alkoxy groups, diphenylamino, naphthylphenylamino, dinaphthylamino, dioxy And diarylamino groups having two aromatic hydrocarbon groups having 6 to 15 carbon atoms such as anthranylamino and diphenanthrenylamino.
- R 1 to R 7 are each independently hydrogen, cyano group, alkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 38 carbon atoms, or 2 to 20 carbon atoms.
- An aromatic hydrocarbon group having 6 to 22 carbon atoms or an aromatic heterocyclic group having 3 to 16 carbon atoms is shown.
- it is an alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a diarylamino group having 12 to 36 carbon atoms, or an aromatic hydrocarbon having 6 to 18 carbon atoms.
- an alkyl group having 1 to 10 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, phenylmethyl, phenylethyl, naphthylmethyl, anthranylmethyl, phenanthrenylmethyl
- An aralkyl group having 7 to 17 carbon atoms such as pyrenylmethyl, an alkoxy group having 1 to 10 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonyloxy, detoxyl, diphenylamino, naphthylphenylamino, Examples thereof include diarylamino groups having 12 to 28 carbon atoms such as dinaphthylamino, dianthranylamino, diphenanthrenylamino and the like.
- aromatic hydrocarbon group having 6 to 22 carbon atoms or the aromatic heterocyclic group having 3 to 16 carbon atoms include benzene, pentalene, indene, naphthalene, azulene, indacene, acenaphthylene, phenalene, phenanthrene, Anthracene, tridene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, pyrene, chrysene, tetraphen, tetracene, pleiaden, picene, perylene, pentaphen, pentacene, tetraphenylene, cholanthrylene, furan, benzofuran, isobenzofuran, xanthene , Oxatolene, dibenzofuran, perixanthenoxanthene, thiophene, thioxanthene, thianthrene, phenoxathiin
- R 1 to R 7 when R 1 to R 7 further have a substituent, the substituent is a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, carbon Alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, dialkylamino group having 2 to 40 carbon atoms, diarylamino group having 12 to 44 carbon atoms, diaralkylamino group having 14 to 76 carbon atoms, carbon number
- it is ⁇ 20 alkylsulfonyl groups.
- An alkyl group having 1 to 10 carbon atoms, an aralkyl group having 7 to 24 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a diarylamino group having 12 to 36 carbon atoms is preferable.
- the number of substituents is preferably 0 to 3 and more preferably 0 to 2 per R 1 to R 7 .
- Hydrogen in the compounds represented by the general formulas (1) and (2) can be replaced with deuterium.
- L 3 each independently represents hydrogen or a monovalent group.
- the monovalent group includes a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and 2 to 2 carbon atoms.
- dialkylamino groups C12-44 diarylamino groups, C14-76 dialkylamino groups, C2-20 acyl groups, C2-20 acyloxy groups, C1-20 carbon atoms
- An alkoxy group having 2 to 20 carbon atoms, an alkoxycarbonyloxy group having 2 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 22 carbon atoms, and 3 to 3 carbon atoms 16 aromatic heterocyclic groups or a linked aromatic group in which 2 to 10 aromatic rings of the aromatic hydrocarbon group and the aromatic heterocyclic group are connected is preferable.
- alkyl groups aralkyl groups, alkenyl groups, alkynyl groups, dialkylamino groups, diarylamino groups, dialkylamino groups, acyl groups, acyloxy groups, alkoxy groups, alkoxycarbonyl groups, alkoxycarbonyloxy groups, alkylsulfonyl groups are as follows.
- R 1 to R 7 wherein 2 to 10 aromatic rings of the aromatic hydrocarbon group, the aromatic heterocyclic group, or the aromatic hydrocarbon group and the aromatic heterocyclic group are linked.
- the linked aromatic group are the same as the specific examples of L 1 and L 2 , and the aromatic hydrocarbon group or aromatic heterocyclic group in L 3 may have a substituent or have a substituent.
- the substituent is a cyano group, an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 38 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an alkynyl group having 2 to 20 carbon atoms.
- At least one of L 3 is preferably a group represented by formula (e1). And it is preferable that the compound represented by General formula (3) is a compound represented by General formula (4).
- L 4 is independently hydrogen, cyano group, alkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 38 carbon atoms, or alkenyl group having 2 to 20 carbon atoms.
- the compound represented by the general formula (4) is preferably a compound represented by the general formula (5).
- E and L 4 are the same as those in the general formula (4).
- L 4 is an alkyl group, aralkyl group, alkenyl group, alkynyl group, dialkylamino group, diarylamino group, dialkylamino group, acyl group, acyloxy group, alkoxy group, alkoxycarbonyl group, alkoxycarbonyloxy group, alkylsulfonyl group, In the case of an aromatic hydrocarbon group, an aromatic heterocyclic group or the like, specific examples thereof are the same as those described for L 3 above.
- E represents oxygen or sulfur. Further, part or all of hydrogen in the compounds represented by the general formulas (3) to (5) can be substituted with deuterium.
- the EA difference between the two host materials is more than 0.1 eV.
- Mixing hosts with an EA difference of 0.1 eV or less does not change the electron injection property to the light emitting layer.
- the electron injection property to the light emitting layer is mixed.
- the transportability in the light emitting layer can be suppressed.
- the EA difference is in the range of 0.2 to 1.5 eV.
- the EA value is obtained by measuring the ionization potential value obtained by photoelectron spectroscopy in the host material thin film and the absorption spectrum in the ultraviolet-visible region, and using the energy gap value obtained from the absorption edge. Can be calculated. However, the measurement method is not limited to this. Although three or more host materials can be used, in this case, the material with the highest EA is (H1), the material with the lowest EA is (H2), and the EA difference is greater than 0.1 eV. Good.
- the two host materials may be mixed before the device is formed and vapor-deposited using one vapor deposition source, or mixed at the time of producing the device by an operation such as co-evaporation using a plurality of vapor deposition sources. It doesn't matter.
- the mixing ratio (weight ratio) of the host material is not particularly limited, but is preferably in the range of 95: 5 to 5:95, more preferably in the range of 90:10 to 10:90.
- the structure of the organic EL element of the present invention will be described with reference to the drawings.
- the structure of the organic EL element of the present invention is not limited to the illustrated one.
- FIG. 1 is a cross-sectional view schematically showing a structural example of a general organic EL element used in the present invention, where 1 is a substrate, 2 is an anode, 3 is a hole injection layer, Reference numeral 4 denotes a hole transport layer, 5 denotes a light emitting layer, 6 denotes an electron transport layer, 7 denotes an electron injection layer, and 8 denotes a cathode.
- the organic EL device of the present invention has an anode, a light emitting layer, an electron transport layer and a cathode as essential layers, but other layers may be provided as necessary. Examples of other layers include, but are not limited to, a hole injection transport layer, an electron blocking layer, and a hole blocking layer.
- a positive hole injection transport layer means either a positive hole injection layer, a positive hole transport layer, or both.
- the substrate 1 serves as a support for the organic electroluminescent element, and a quartz or glass plate, a metal plate or a metal foil, a plastic film or a sheet is used.
- glass plates and smooth and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate and polysulfone are preferred.
- a synthetic resin substrate it is necessary to pay attention to gas barrier properties. If the gas barrier property of the substrate is too small, the organic electroluminescent element may be deteriorated by the outside air that has passed through the substrate, which is not preferable. For this reason, a method of providing a gas barrier property by providing a dense silicon oxide film or the like on at least one surface of the synthetic resin substrate is also a preferable method.
- Anode An anode 2 is provided on the substrate 1, and the anode plays a role of hole injection into the hole transport layer.
- This anode is usually a metal such as aluminum, gold, silver, nickel, palladium, platinum, a metal oxide such as an oxide of indium and / or tin, an oxide of indium and / or zinc, or a halogen such as copper iodide.
- Metal oxide, carbon black, or a conductive polymer such as poly (3-methylthiophene), polypyrrole, or polyaniline.
- the anode is often formed by a sputtering method, a vacuum deposition method, or the like.
- anode can also be formed by coating.
- a conductive polymer a thin film can be directly formed on a substrate by electrolytic polymerization, or an anode can be formed by applying a conductive polymer on the substrate 1 (Appl. Phys. Lett., 60). (Vol. 2711, 1992).
- the anode can be formed by stacking different materials. The thickness of the anode varies depending on the required transparency.
- the visible light transmittance is usually 60% or more, preferably 80% or more.
- the thickness is usually 5 to 1000 nm, preferably 10 to 10%. It is about 500 nm.
- the anode may be the same as the substrate. Furthermore, it is also possible to laminate different conductive materials on the anode.
- the hole transport layer 4 is provided on the anode 2.
- a hole injection layer 3 can also be provided between them.
- the material of the hole transport layer it is necessary that the material has a high hole injection efficiency from the anode and can efficiently transport the injected holes.
- the ionization potential is low, the transparency to visible light is high, the hole mobility is high, the stability is high, and impurities that become traps are unlikely to be generated during manufacturing or use.
- the light emitting layer 5 it is required not to quench the light emitted from the light emitting layer or to form an exciplex with the light emitting layer to reduce the efficiency.
- the element is further required to have heat resistance. Therefore, a material having a Tg value of 85 ° C. or higher is desirable.
- hole transporting material that can be used in the present invention
- known compounds conventionally used in this layer can be used.
- an aromatic diamine containing two or more tertiary amines and having two or more condensed aromatic rings substituted with nitrogen atoms Japanese Patent Laid-Open No. 5-234681
- 4,4 ', 4 "-tris (1- Aromatic amine compounds having a starburst structure such as naphthylphenylamino) triphenylamine
- aromatic amine compounds comprising a tetramer of triphenylamine
- spiro compounds such as 2,2 ', 7,7'-tetrakis- (diphenylamino) -9,9'-spirobifluorene (Synth. Metals, 91, 209) Page, 1997), etc. These compounds may be used alone or in combination as necessary.
- polyarylene ether sulfone Polym. Adv. Tech
- polyvinylcarbazole polyvinyltriphenylamine
- tetraphenylbenzidine as a material for the hole transport layer. ., Vol. 7, p. 33, 1996).
- the hole transport layer When forming the hole transport layer by a coating method, one or more hole transport materials and, if necessary, an additive such as a binder resin or a coating property improving agent that does not trap holes are added, Dissolve to prepare a coating solution, apply onto the anode by a method such as spin coating, and dry to form a hole transport layer.
- the binder resin include polycarbonate, polyarylate, and polyester.
- the hole transport material When forming by vacuum evaporation, put the hole transport material in a crucible installed in a vacuum vessel, evacuate the vacuum vessel to about 10 -4 Pa with a suitable vacuum pump, then heat the crucible The hole transport material is evaporated, and a hole transport layer is formed on the substrate on which the anode is formed, facing the crucible.
- the thickness of the hole transport layer is usually 1 to 300 nm, preferably 5 to 100 nm. In order to uniformly form such a thin film, a vacuum deposition method is generally used.
- the hole injection layer is provided between the hole transport layer 4 and the anode 2. 3 is also inserted.
- the driving voltage of the initial element is lowered, and at the same time, an increase in voltage when the element is continuously driven with a constant current is suppressed.
- the conditions required for the material used for the hole injection layer are that the contact with the anode is good and a uniform thin film can be formed, which is thermally stable, that is, the glass transition temperature is high, and the glass transition temperature is 100 ° C. or higher. Is required. Furthermore, the ionization potential is low, hole injection from the anode is easy, and the hole mobility is high.
- phthalocyanine compounds such as copper phthalocyanine (Japanese Patent Laid-Open No. 63-295695), polyaniline (Appl. Phys. Lett., 64, 1245, 1994), polythiophene (Optical Materials, (9, 125, 1998) organic compounds such as sputtered carbon films (Synth. Met., 91, 73, 1997), metals such as vanadium oxide, ruthenium oxide, molybdenum oxide P-types such as oxides (J. Phys. D, Vol.
- a thin film can be formed in the same manner as the hole transport layer, but in the case of an inorganic material, a sputtering method, an electron beam evaporation method, or a plasma CVD method is further used.
- the thickness of the hole injection layer formed as described above is usually 1 to 300 nm, preferably 5 to 100 nm.
- the light-emitting layer 5 is provided on the hole transport layer 4.
- the light emitting layer may be formed from a single light emitting layer, or may be formed by laminating a plurality of light emitting layers so as to be in direct contact with each other.
- the light emitting layer contains at least two host materials and a light emitting dopant.
- the luminescent dopant may be a fluorescent luminescent material or a phosphorescent luminescent material.
- the at least two host materials are a combination of at least one compound of the general formula (1) or (2) and at least one compound of the general formula (3).
- condensed ring derivatives such as perylene and rubrene, quinacridone derivatives, phenoxazone 660, DCM1, perinone, coumarin derivatives, pyromethene (diazaindacene) derivatives, cyanine dyes and the like can be used.
- a material containing an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold is preferable. Specific examples include compounds described in the following patent documents, but are not limited to these compounds.
- Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 ⁇ acac3, and complexes such as PtOEt3. Specific examples of these complexes are shown below, but are not limited to the following compounds.
- the amount of the phosphorescent dopant contained in the light emitting layer is 2 to 40% by weight, preferably 5 to 30% by weight.
- the film thickness of the light emitting layer is not particularly limited, but is usually 1 to 300 nm, preferably 5 to 100 nm, and is formed into a thin film by the same method as the hole transport layer.
- Electron transport layer 6 An electron transport layer 6 is provided between the light emitting layer 5 and the cathode 8 for the purpose of further improving the light emission efficiency of the device.
- the electron transport layer an electron transport material capable of smoothly injecting electrons from the cathode is preferable, and any commonly used material can be used.
- a metal complex such as Alq3 (JP 59-194393A), a metal complex of 10-hydroxybenzo [h] quinoline, an oxadiazole derivative, a distyrylbiphenyl derivative, a silole derivative, 3 -Or 5-hydroxyflavone metal complex, benzoxazole metal complex, benzothiazole metal complex, trisbenzimidazolylbenzene (USP 5,645,948), quinoxaline compound (JP6-207169A), phenanthroline derivative (JP5-331459A), 2-t-butyl- 9,10-N, N′-dicyanoanthraquinone diimine, n-type hydrogenated amorphous silicon carbide, n-type zinc sulfide, n-type zinc selenide and the like.
- the film thickness of the electron transport layer is usually 1 to 300 nm, preferably 5 to 100 nm.
- the electron transport layer is formed by laminating on the light emitting layer by a coating method or a vacuum deposition method in the same manner as the hole transport layer. Usually, a vacuum deposition method is used.
- the cathode 8 plays a role of injecting electrons into the electron transport layer 6.
- the material used for the anode 2 can be used.
- a metal having a low work function is preferable for efficient electron injection, and tin, magnesium, indium, calcium, aluminum
- a suitable metal such as silver or an alloy thereof is used.
- Specific examples include low work function alloy electrodes such as magnesium-silver alloy, magnesium-indium alloy, and aluminum-lithium alloy.
- the thickness of the cathode is usually the same as that of the anode.
- a metal layer having a high work function and stable to the atmosphere on the cathode increases the stability of the device.
- metals such as aluminum, silver, copper, nickel, chromium, gold, platinum are used.
- inserting an ultra-thin insulating film (0.1-5 nm) such as LiF, MgF 2 , Li 2 O between the cathode 8 and the electron transport layer 6 as the electron injection layer 7 is effective in improving the efficiency of the device. Is the method.
- a cathode 8 an electron injection layer 7, an electron transport layer 6, a light emitting layer 5, a hole transport layer 4, a hole injection layer 3, and an anode 2 are laminated on the substrate 1 in this order. It is also possible to provide the organic EL element of the present invention between two substrates, at least one of which is highly transparent as described above. Also in this case, layers can be added or omitted as necessary.
- the organic EL element of the present invention can be any of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix.
- the light emitting layer is a mixed host composed of two host materials, and a specific compound is used as at least one of the host materials, so that the luminous efficiency is high even at a low voltage.
- a device with greatly improved driving stability can be obtained, and excellent performance can be exhibited in application to full-color or multi-color panels.
- Example 1 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 4 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 150 nm was formed.
- copper phthalocyanine (CuPc) is formed to a thickness of 20 nm on ITO as a hole injection layer, and then 4,4-bis [N- (1-naphthyl) -N-phenylamino] is formed as a hole transport layer.
- Biphenyl (NPB) was formed to a thickness of 20 nm.
- compound 1-2 as the first host, compound 3-87 as the second host, and tris (2-phenylpyridine) iridium (III) (Ir (PPy) 3 ) as the light emitting layer guest, respectively.
- co-deposited from different deposition sources and formed to a thickness of 30 nm.
- the deposition rate ratio of the first host, the second host, and Ir (PPy) 3 (volume rate ratio of the vaporized product) was 47: 47: 6.
- aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (BAlq) was formed to a thickness of 10 nm as a hole blocking layer.
- Example 1 the organic EL element was produced like Example 1 except having used the compound described in Table 1 as a light emitting layer 2nd host.
- an external power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 517 nm was observed from any organic EL element, and light emission from Ir (PPy) 3 was obtained.
- Table 1 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that the compound described in Table 1 was used alone as the light emitting layer host.
- the host amount was the same as the total of the first host and the second host in Example 1, and the guest amount was the same.
- a power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 517 nm was observed from any organic EL element, and light emission from Ir (PPy) 3 was obtained. all right.
- Table 1 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Table 1 shows the luminance, external quantum efficiency, and luminance half-life of the produced organic EL element.
- Luminance and external quantum efficiency are values at a driving current of 2.5 mA / cm 2 and are initial characteristics.
- the luminance half time is a value at an initial luminance of 1000 cd / m 2 .
- the compound number is the number given to the above chemical formula.
- H1 is a first host and H2 is a second host.
- Luminance and external quantum efficiency are initial characteristics, and luminance half-life is a lifetime characteristic.
- the deposition rate ratio of the first host, the second host, and Ir (PPy) 3 was 47: 47: 6.
- BAlq was formed to a thickness of 10 nm as a hole blocking layer.
- Alq 3 was formed to a thickness of 40nm as an electron transport layer.
- lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer.
- Al was formed as a cathode to a thickness of 100 nm to produce an organic EL element.
- Comparative Example 7 Moreover, the organic EL element which used the following compound A alone as a light emitting layer host was produced similarly. When an external power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 517 nm was observed from both organic EL elements, and it was found that light emission from Ir (PPy) 3 was obtained. It was. Table 1 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- the mixed host of Compound 1-2 and Compound A is compared with the single host of Compound A and the single host of Compound 1-2 (Comparative Example 1). It can be seen that the luminance and external quantum efficiency are improved by using the light emitting layer host, but the luminance half time is shortened. From this result, it was found that when a mixed host of compounds other than the specific skeleton is used as the light emitting layer host, the drive life characteristics may be deteriorated.
- Example 5 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 4 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 150 nm was formed.
- CuPc is formed as a hole injection layer on ITO to a thickness of 25 nm
- NPB is formed as a first hole transport layer to a thickness of 10 nm
- 4, 4 as a second hole transport layer.
- ', 4''-Tris (N-carbazolyl) -triphenylamine (TCTA) was formed to a thickness of 10 nm.
- compound 1-114 as the first host compound 3-87 as the second host, tris [1- (4′-cyanophenyl) -3-methylbenzimidazole-2- Iriden-C 2 , C 2 ′ ] -iridium (III) (Ir (cn-pmic) 3 ) was co-deposited from different deposition sources to form a thickness of 30 nm.
- the deposition rate ratio of the first host, the second host, and Ir (cn-pmic) 3 was 45:45:10.
- BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
- Alq 3 was formed to a thickness of 25 nm as an electron transport layer. Further, on the electron transport layer, lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer. Finally, on the electron injection layer, aluminum (Al) was formed as a cathode to a thickness of 100 nm to produce an organic EL element. When an external power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 460 nm was observed, and it was found that light emission from Ir (cn-pmic) 3 was obtained. Table 2 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Example 6 an organic EL device was produced in the same manner as in Example 5 except that Compound 3-88 was used as the second host of the light emitting layer.
- Compound 3-88 was used as the second host of the light emitting layer.
- an external power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 460 nm was observed from any organic EL element, and light emission from Ir (cn-pmic) 3 was obtained. I found out.
- Table 2 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Example 7 An organic EL device was produced in the same manner as in Example 5, except that Compound 2-9 was used as the first host for light emission and Compound 3-87 was used as the second host for light emitting layer.
- Compound 2-9 was used as the first host for light emission
- Compound 3-87 was used as the second host for light emitting layer.
- an external power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 460 nm was observed from any organic EL element, and light emission from Ir (cn-pmic) 3 was obtained. I found out.
- Table 2 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Example 8 An organic EL device was produced in the same manner as in Example 5 except that Compound 2-9 was used as the first host for light emission and Compound 3-88 was used as the second host for light emitting layer.
- Compound 2-9 was used as the first host for light emission
- Compound 3-88 was used as the second host for light emitting layer.
- an external power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 460 nm was observed from any organic EL element, and light emission from Ir (cn-pmic) 3 was obtained. I found out.
- Table 2 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Example 5 an organic EL device was produced in the same manner as in Example 5 except that the compound described in Table 2 was used alone as the light emitting layer host.
- the host amount was the same as the total of the first host and the second host in Example 5, and the guest amount was the same.
- a power source was connected to the obtained organic EL element and a DC voltage was applied, an emission spectrum with a maximum wavelength of 460 nm was observed from any organic EL element, and light emission from Ir (cn-pmic) 3 was obtained. I understood it.
- Table 2 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Table 2 shows the luminance, external quantum efficiency, and luminance half-life of the organic EL device produced.
- Luminance and external quantum efficiency are values at a driving current of 2.5 mA / cm 2 and are initial characteristics.
- the luminance half time is a value at an initial luminance of 1000 cd / m 2 .
- the organic EL element of the present invention is a flat panel display (mobile phone display element, vehicle-mounted display element, OA computer display element, television, etc.), and a light source (illumination, light source of a copying machine, liquid crystal display) utilizing the characteristics as a surface light emitter.
- a light source illumination, light source of a copying machine, liquid crystal display
- its technical value is great in applications to backlights for measuring instruments, display boards, indicator lamps, and the like.
Abstract
Description
環b、環d、環d’はそれぞれ独立に2つの隣接環の任意の位置で縮合する式(b1)で表される複素環を示し、
X1はCR7又はNを示し、
Ar1、Ar2はそれぞれ独立に炭素数6~22の芳香族炭化水素基、又は炭素数3~6の単環の芳香族複素環基を示し、
Zは炭素数6~22の芳香族炭化水素基、炭素数3~16の芳香族複素環基、又は該芳香族炭化水素基及び芳香族複素環基の芳香族環が2~10連結してなる連結芳香族基から選ばれる2価の連結基を表すが、Nに連結する基は炭素数6~22の芳香族炭化水素基又は炭素数3~6の単環の芳香族複素環基である。
R1~R7はそれぞれ独立に、水素、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、炭素数1~20のアルキルスルホニル基、炭素数6~22の芳香族炭化水素基又は炭素数3~16の芳香族複素環基を示し、
L1、L2はそれぞれ独立に炭素数6~22の芳香族炭化水素基、炭素数3~16の芳香族複素環基、又は該芳香族炭化水素基及び芳香族複素環基の芳香族環が2~10個連結された連結芳香族基を示し、
p、qは0~7の整数を示し、h、i、j、k、l及びmは4の整数を示し、nは2の整数を示し、L1、L2、及びR1~R7が複数ある場合は、それぞれ同一でも異なってもよく、上記Ar1、Ar2 、L1、L2、Z、及びR1~R7における芳香族炭化水素基又は芳香族複素環基は、置換基を有してもよく、置換基を有する場合の置換基は、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、又は炭素数1~20のアルキルスルホニル基である。
X2はそれぞれ独立してCL4又は窒素を表し、複数のL4は同一であっても異なっていてもよく、
L4における芳香族炭化水素基又は芳香族複素環基は、置換基を有してもよく、置換基を有する場合の置換基は、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、又は炭素数1~20のアルキルスルホニル基である。
(式中、L4、及びEは、一般式(4)中のL4、及びEと同意である。)
p、qは0~7の整数を示し、好ましくは0~5であり、より好ましくは0~3である。h、i、j、k、l及びmは4の整数を示し、nは2の整数を示す。L1、L2、及びR1~R7が複数ある場合は、それぞれ同一でも異なってもよい。
図1は本発明に用いられる一般的な有機EL素子の構造例を模式的に示す断面図であり、1は基板、2は陽極、3は正孔注入層、4は正孔輸送層、5は発光層、6は電子輸送層、7は電子注入層、8は陰極を各々示す。本発明の有機EL素子では、陽極、発光層、電子輸送層及び陰極を必須の層として有するが、必要により他の層を設けてもよい。他の層とは、例えば正孔注入輸送層や電子阻止層及び正孔阻止層が挙げられるが、これらに限定されるものではない。なお、正孔注入輸送層は、正孔注入層と正孔輸送層のいずれか又は両者を意味する。
基板1は有機電界発光素子の支持体となるものであり、石英やガラスの板、金属板や金属箔、プラスチックフィルムやシートなどが用いられる。特にガラス板や、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホンなどの平滑で透明な合成樹脂の板が好ましい。合成樹脂基板を使用する場合にはガスバリア性に留意する必要がある。基板のガスバリア性が小さすぎると、基板を通過した外気により有機電界発光素子が劣化することがあるので好ましくない。このため、合成樹脂基板の少なくとも片面に緻密なシリコン酸化膜等を設けてガスバリア性を確保する方法も好ましい方法の一つである。
基板1上には陽極2が設けられるが、陽極は正孔輸送層への正孔注入の役割を果たすものである。この陽極は、通常、アルミニウム、金、銀、ニッケル、パラジウム、白金等の金属、インジウム及び/又はスズの酸化物、インジウム及び/又は亜鉛の酸化物などの金属酸化物、ヨウ化銅などのハロゲン化金属、カーボンブラック、あるいは、ポリ(3-メチルチオフェン)、ポリピロール、ポリアニリン等の導電性高分子などにより構成される。陽極の形成は通常、スパッタリング法、真空蒸着法などにより行われることが多い。また、銀などの金属微粒子、ヨウ化銅などの微粒子、カーボンブラック、導電性の金属酸化物微粒子、導電性高分子微粉末などの場合には、適当なバインダー樹脂溶液に分散し、基板上に塗布することにより陽極を形成することもできる。更に、導電性高分子の場合は電解重合により直接基板上に薄膜を形成したり、基板1上に導電性高分子を塗布して陽極を形成することもできる(Appl.Phys.Lett.,60巻,2711頁,1992年)。陽極は異なる物質で積層して形成することも可能である。陽極の厚みは、必要とする透明性により異なる。透明性が必要とされる場合は、可視光の透過率を、通常、60%以上、好ましくは80%以上とすることが望ましく、この場合、厚みは、通常、5~1000nm、好ましくは10~500nm程度である。不透明でよい場合には、陽極は基板と同一でもよい。また、更には上記の陽極の上に異なる導電材料を積層することも可能である。
陽極2の上に正孔輸送層4が設けられる。両者の間には、正孔注入層3を設けることもできる。正孔輸送層の材料に要求される条件としては、陽極からの正孔注入効率が高く、かつ、注入された正孔を効率よく輸送することができる材料であることが必要である。そのためには、イオン化ポテンシャルが小さく、可視光の光に対して透明性が高く、しかも正孔移動度が大きく、更に安定性に優れ、トラップとなる不純物が製造時や使用時に発生しにくいことが要求される。また、発光層5に接するために発光層からの発光を消光したり、発光層との間でエキサイプレックスを形成して効率を低下させないことが求められる。上記の一般的要求以外に、車載表示用の応用を考えた場合、素子には更に耐熱性が要求される。従って、Tgとして85℃以上の値を有する材料が望ましい。
また、上記の化合物以外に、正孔輸送層の材料として、ポリビニルカルバゾール、ポリビニルトリフェニルアミン(特開平7-53953号公報)、テトラフェニルベンジジンを含有するポリアリーレンエーテルサルホン(Polym. Adv. Tech., 7巻、33頁、1996年)等の高分子材料が挙げられる。
正孔注入の効率を更に向上させ、かつ、有機層全体の陽極への付着力を改善させる目的で、正孔輸送層4と陽極2との間に正孔注入層3を挿入することも行われている。正孔注入層を挿入することで、初期の素子の駆動電圧が下がると同時に、素子を定電流で連続駆動した時の電圧上昇も抑制される効果がある。正孔注入層に用いられる材料に要求される条件としては、陽極とのコンタクトがよく均一な薄膜が形成でき、熱的に安定、すなわち、ガラス転移温度が高く、ガラス転移温度としては100℃以上が要求される。更に、イオン化ポテンシャルが低く陽極からの正孔注入が容易なこと、正孔移動度が大きいことが挙げられる。
正孔輸送層4の上に発光層5が設けられる。発光層は、単一の発光層から形成されていてもよいし、複数の発光層を直接接するように積層して構成されていてもよい。発光層は、少なくとも2つのホスト材料と発光性ドーパントを含有する。発光性ドーパントは、蛍光性発光材料又は燐光性発光材料であることがよい。少なくとも2つのホスト材料は、一般式(1)又は(2)の化合物の少なくとも1つと、一般式(3)の化合物の少なくとも1つの組み合わせである。
素子の発光効率を更に向上させることを目的として、発光層5と陰極8の間に、電子輸送層6が設けられる。電子輸送層としては、陰極からスムーズに電子を注入できる電子輸送性材料が好ましく、一般的に使用される任意の材料を用いることができる。このような条件を満たす電子輸送材料としては、Alq3などの金属錯体(JP 59-194393A)、10-ヒドロキシベンゾ[h]キノリンの金属錯体、オキサジアゾール誘導体、ジスチリルビフェニル誘導体、シロール誘導体、3-又は5-ヒドロキシフラボン金属錯体、ベンズオキサゾール金属錯体、ベンゾチアゾール金属錯体、トリスベンズイミダゾリルベンゼン(USP 5,645,948)、キノキサリン化合物(JP6-207169A)、フェナントロリン誘導体(JP5-331459A)、2-t-ブチル-9,10-N,N'-ジシアノアントラキノンジイミン、n型水素化非晶質炭化シリコン、n型硫化亜鉛、n型セレン化亜鉛などが挙げられる。
陰極8は、電子輸送層6に電子を注入する役割を果たす。陰極として用いられる材料は、前記陽極2に使用される材料を用いることが可能であるが、効率よく電子注入を行なうには、仕事関数の低い金属が好ましく、スズ、マグネシウム、インジウム、カルシウム、アルミニウム、銀等の適当な金属又はそれらの合金が用いられる。具体例としては、マグネシウム-銀合金、マグネシウム-インジウム合金、アルミニウム-リチウム合金等の低仕事関数合金電極が挙げられる。
陰極の膜厚は通常、陽極と同様である。低仕事関数金属からなる陰極を保護する目的で、この上に更に、仕事関数が高く大気に対して安定な金属層を積層することは素子の安定性を増す。この目的のために、アルミニウム、銀、銅、ニッケル、クロム、金、白金等の金属が使われる。
更に、電子注入層7として、陰極8と電子輸送層6の間にLiF 、MgF2、Li2O等の極薄絶縁膜(0.1~5nm)を挿入することも素子の効率を向上させる有効な方法である。
膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4Paで積層させた。まず、ITO上に正孔注入層として銅フタロシアニン(CuPc)を20nmの厚さに形成し、次に正孔輸送層として4,4-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(NPB)を20nmの厚さに形成した。次に発光層として、第一ホストとして化合物1-2を、第二ホストとして化合物3‐87を、発光層ゲストとしてトリス(2-フェニルピリジン)イリジウム(III)(Ir(PPy)3)をそれぞれ異なる蒸着源から共蒸着し、30nmの厚さに形成した。この時、第一ホストと第二ホストとIr(PPy)3の蒸着速度比(気化物の体積速度比)は、47:47:6であった。次に、正孔阻止層としてアルミニウム(III)ビス(2-メチル-8-キノリナト)4-フェニルフェノラート(BAlq)を10nmの厚さに形成した。次に、電子輸送層としてトリス-(8-ヒドロキシキノリナト)アルミニウム(III)(Alq3)を40nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、陰極としてアルミニウム(Al)を100nmの厚さに形成し、有機EL素子を作製した。
得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、極大波長517nmの発光スペクトルが観測され、Ir(PPy)3からの発光が得られていることがわかった。表1に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
実施例1において、発光層第二ホストとして表1に記載した化合物を用いた以外は実施例1と同様にして有機EL素子を作製した。得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、いずれの有機EL素子からも極大波長517nmの発光スペクトルが観測され、Ir(PPy)3からの発光が得られていることがわかった。表1に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
実施例1において、発光層ホストとして表1に記載した化合物を単独で用いた以外は実施例1と同様にして有機EL素子を作製した。なお、ホスト量は、実施例1における第1ホストと第2ホストの合計と同じ量とし、ゲスト量は同様とした。得られた有機EL素子に電源を接続し直流電圧を印加したところ、いずれの有機EL素子からも極大波長517nmの発光スペクトルが観測され、Ir(PPy)3からの発光が得られていることがわかった。表1に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4Paで積層させた。まず、ITO上に正孔注入層としてCuPcを20nmの厚さに形成し、次に正孔輸送層としてNPBを20nmの厚さに形成した。次に発光層として、第一ホストとして化合物1‐2を、第二ホストとして以下に示す化合物Aを、発光層ゲストとしてIr(PPy)3をそれぞれ異なる蒸着源から共蒸着し、30nmの厚さに形成した。この時、第一ホストと第二ホストとIr(PPy)3の蒸着速度比は、47:47:6であった。次に、正孔阻止層としてBAlqを10nmの厚さに形成した。次に、電子輸送層としてAlq3を40nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、陰極としてアルミニウム(Al)を100nmの厚さに形成し、有機EL素子を作製した。
また、発光層ホストとして下記化合物Aを単独で用いた有機EL素子も同様に作製した。
得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、両有機EL素子から極大波長517nmの発光スペクトルが観測され、Ir(PPy)3からの発光が得られていることがわかった。表1に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4Paで積層させた。まず、ITO上に正孔注入層としてCuPcを25nmの厚さに形成し、次に第一正孔輸送層としてNPBを10nmの厚さに形成し、さらに第二正孔輸送層として4,4’,4’’-トリス(N-カルバゾリル)-トリフェニルアミン(TCTA)を10nmの厚さに形成した。次に発光層として、第一ホストとして化合物1‐114を、第二ホストとして化合物3‐87を、発光層ゲストとしてトリス[1-(4′-シアノフェニル)-3-メチルベンゾイミダゾール-2-イリデン-C2、C2']-イリジウム(III)(Ir(cn-pmic)3)をそれぞれ異なる蒸着源から共蒸着し、30nmの厚さに形成した。この時、第一ホストと第二ホストとIr(cn-pmic)3の蒸着速度比は、45:45:10であった。次に、正孔阻止層として2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン(BCP)を10nmの厚さに形成した。次に、電子輸送層としてAlq3を25nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、陰極としてアルミニウム(Al)を100nmの厚さに形成し、有機EL素子を作製した。
得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、極大波長460nmの発光スペクトルが観測され、Ir(cn-pmic)3からの発光が得られていることがわかった。表2に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
実施例5において、発光層第二ホストとして化合物3‐88を用いた以外は実施例5と同様にして有機EL素子を作製した。得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、いずれの有機EL素子からも極大波長460nmの発光スペクトルが観測され、Ir(cn-pmic)3からの発光が得られていることがわかった。表2に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
実施例5において、発光第一ホストとして化合物2-9を、発光層第二ホストとして化合物3‐87を用いた以外は実施例5と同様にして有機EL素子を作製した。得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、いずれの有機EL素子からも極大波長460nmの発光スペクトルが観測され、Ir(cn-pmic)3からの発光が得られていることがわかった。表2に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
実施例5において、発光第一ホストとして化合物2-9を、発光層第二ホストとして化合物3‐88を用いた以外は実施例5と同様にして有機EL素子を作製した。得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、いずれの有機EL素子からも極大波長460nmの発光スペクトルが観測され、Ir(cn-pmic)3からの発光が得られていることがわかった。表2に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
実施例5において、発光層ホストとして表2に記載した化合物を単独で用いた以外は実施例5と同様にして有機EL素子を作製した。なお、ホスト量は、実施例5における第1ホストと第2ホストの合計と同じ量とし、ゲスト量は同様とした。得られた有機EL素子に電源を接続し直流電圧を印加したところ、いずれの有機EL素子からも極大波長460nmの発光スペクトルが観測され、Ir(cn-pmic)3からの発光が得られていることがわかった。表2に作製した有機EL素子の輝度、外部量子効率及び輝度半減寿命を示す。
Claims (7)
- 対向する陽極と陰極の間に、1つ以上の発光層を含む有機電界発光素子において、少なくとも1つの発光層が少なくとも2つのホスト材料と少なくとも1つの発光性ドーパントを含有し、該少なくとも2つのホスト材料は、下記一般式(1)~(2)のいずれかで表される化合物から選ばれる材料と、下記一般式(3)で表される化合物から選ばれる材料であることを特徴とする有機電界発光素子。
ここで、環a、環c、環c’はそれぞれ独立に2つの隣接環の任意の位置で縮合する式(a1)で表される芳香環又は複素環を示し、
環b、環d、環d’はそれぞれ独立に2つの隣接環の任意の位置で縮合する式(b1)で表される複素環を示し、
X1はCR7又はNを示し、
Ar1、Ar2はそれぞれ独立に炭素数6~22の芳香族炭化水素基、又は炭素数3~6の単環の芳香族複素環基を示し、
Zは炭素数6~22の芳香族炭化水素基、炭素数3~16の芳香族複素環基、又は該芳香族炭化水素基及び芳香族複素環基の芳香族環が2~10連結してなる連結芳香族基から選ばれる2価の連結基を表すが、Nに結合する基は炭素数6~22の芳香族炭化水素基又は炭素数3~6の単環の芳香族複素環基である。
R1~R7はそれぞれ独立に、水素、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、炭素数1~20のアルキルスルホニル基、炭素数6~22の芳香族炭化水素基又は炭素数3~16の芳香族複素環基を示し、
L1、L2はそれぞれ独立に炭素数6~22の芳香族炭化水素基、炭素数3~16の芳香族複素環基、又は該芳香族炭化水素基及び芳香族複素環基の芳香族環が2~10個連結された連結芳香族基を示し、
p、qは0~7の整数を示し、h、i、j、k、l及びmは4の整数を示し、nは2の整数を示し、L1、L2、及びR1~R7が複数ある場合は、それぞれ同一でも異なってもよい。上記Ar1、Ar2、L1、L2、Z、及びR1~R7における芳香族炭化水素基又は芳香族複素環基は、置換基を有してもよく、置換基を有する場合の置換基は、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、又は炭素数1~20のアルキルスルホニル基である。
ここで、L3はそれぞれ独立して水素、又は1価の基を表し、Eは酸素又は硫黄を表す。 - 一般式(1)~(2)のいずれかで表される化合物から選ばれる材料と、一般式(3)で表される化合物から選ばれる材料の電子親和力の差(ΔEA)が0.1eVより大きい請求項1に記載の有機電界発光素子。
- 一般式(1)~(2)中、Ar1又はAr2の少なくとも一つが炭素数3~6の単環の芳香族複素環基であり、X1がCR7である請求項1に記載の有機電界発光素子。
- 一般式(3)中のL3の少なくとも1つが式(e1)で表される1価の基である請求項1に記載の有機電界発光素子。
ここで、L4はそれぞれ独立して水素、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、炭素数1~20のアルキルスルホニル基、炭素数6~22の芳香族炭化水素基又は炭素数3~16の芳香族複素環基、又は該芳香族炭化水素基及び芳香族複素環基の芳香族環が2~10個連結された連結芳香族基を表し、
X2はそれぞれ独立してCL4又は窒素を表し、
L4における芳香族炭化水素基又は芳香族複素環基は、置換基を有してもよく、置換基を有する場合の置換基は、シアノ基、炭素数1~20のアルキル基、炭素数7~38のアラルキル基、炭素数2~20のアルケニル基、炭素数2~20のアルキニル基、炭素数2~40のジアルキルアミノ基、炭素数12~44のジアリールアミノ基、炭素数14~76のジアルキルアミノ基、炭素数2~20のアシル基、炭素数2~20のアシルオキシ基、炭素数1~20のアルコキシ基、炭素数2~20のアルコキシカルボニル基、炭素数2~20のアルコキシカルボニルオキシ基、又は炭素数1~20のアルキルスルホニル基である。 - 発光性ドーパントが、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金属錯体からなる燐光発光ドーパントであることを特徴とする請求項1に記載の有機電界発光素子。
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WO2016158363A1 (ja) * | 2015-03-30 | 2016-10-06 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
CN107431140A (zh) * | 2015-03-30 | 2017-12-01 | 新日铁住金化学株式会社 | 有机电致发光元件 |
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JPWO2016158363A1 (ja) * | 2015-03-30 | 2018-03-15 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
EP3279961A4 (en) * | 2015-03-30 | 2018-11-21 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
TWI675024B (zh) * | 2015-03-30 | 2019-10-21 | 日商日鐵化學材料股份有限公司 | 有機電致發光元件 |
KR102553284B1 (ko) * | 2015-03-30 | 2023-07-07 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계 발광 소자 |
JP2018520513A (ja) * | 2015-06-26 | 2018-07-26 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 多成分ホスト材料及びそれを含む有機電界発光デバイス |
Also Published As
Publication number | Publication date |
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EP2933851A4 (en) | 2016-07-27 |
CN104885247B (zh) | 2017-05-10 |
TW201432025A (zh) | 2014-08-16 |
US20150325796A1 (en) | 2015-11-12 |
TWI592464B (zh) | 2017-07-21 |
KR20150097703A (ko) | 2015-08-26 |
KR102160720B1 (ko) | 2020-09-28 |
EP2933851B1 (en) | 2017-05-10 |
US10361378B2 (en) | 2019-07-23 |
EP2933851A1 (en) | 2015-10-21 |
JPWO2014097813A1 (ja) | 2017-01-12 |
CN104885247A (zh) | 2015-09-02 |
JP6357422B2 (ja) | 2018-07-11 |
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