WO2012141249A1 - Organic electroluminescent element - Google Patents
Organic electroluminescent element Download PDFInfo
- Publication number
- WO2012141249A1 WO2012141249A1 PCT/JP2012/060027 JP2012060027W WO2012141249A1 WO 2012141249 A1 WO2012141249 A1 WO 2012141249A1 JP 2012060027 W JP2012060027 W JP 2012060027W WO 2012141249 A1 WO2012141249 A1 WO 2012141249A1
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- WIPO (PCT)
- Prior art keywords
- general formula
- group
- substituent
- carbon atoms
- hydrogen atom
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 210
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 116
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 289
- 239000010410 layer Substances 0.000 claims description 289
- 239000000463 material Substances 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 106
- 125000000217 alkyl group Chemical group 0.000 claims description 84
- 239000012044 organic layer Substances 0.000 claims description 83
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 125000001153 fluoro group Chemical group F* 0.000 claims description 33
- 239000000758 substrate Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 229910052731 fluorine Inorganic materials 0.000 claims description 28
- 238000005401 electroluminescence Methods 0.000 claims description 21
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 12
- 150000001555 benzenes Chemical group 0.000 claims description 7
- 238000005286 illumination Methods 0.000 claims description 7
- 125000005647 linker group Chemical group 0.000 claims description 6
- 238000001771 vacuum deposition Methods 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 4
- 125000005577 anthracene group Chemical group 0.000 claims description 3
- 230000006866 deterioration Effects 0.000 abstract description 14
- 230000008859 change Effects 0.000 abstract description 12
- -1 n-octyl Chemical group 0.000 description 74
- 238000002347 injection Methods 0.000 description 52
- 239000007924 injection Substances 0.000 description 52
- 125000004093 cyano group Chemical group *C#N 0.000 description 37
- 125000000623 heterocyclic group Chemical group 0.000 description 28
- 239000010408 film Substances 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 230000000903 blocking effect Effects 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 0 C*c1c(*C)c2c(*)c(*C(***(C)*3)=C3c3c(*)c(*)c4c(*C)c5*C)c3c4c2c5c1* Chemical compound C*c1c(*C)c2c(*)c(*C(***(C)*3)=C3c3c(*)c(*)c4c(*C)c5*C)c3c4c2c5c1* 0.000 description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 19
- 125000003277 amino group Chemical group 0.000 description 17
- 125000003367 polycyclic group Chemical group 0.000 description 17
- 125000004104 aryloxy group Chemical group 0.000 description 15
- 150000001721 carbon Chemical group 0.000 description 15
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- 239000002184 metal Substances 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 238000000746 purification Methods 0.000 description 12
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- 230000000052 comparative effect Effects 0.000 description 11
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
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- 238000000295 emission spectrum Methods 0.000 description 9
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- 125000005010 perfluoroalkyl group Chemical group 0.000 description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 238000000149 argon plasma sintering Methods 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- 239000000543 intermediate Substances 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
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- 239000000853 adhesive Substances 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
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- 238000004440 column chromatography Methods 0.000 description 4
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- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000002541 furyl group Chemical group 0.000 description 3
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- 125000001786 isothiazolyl group Chemical group 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
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- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 3
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
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- 238000004544 sputter deposition Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Definitions
- X represents CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b jointly form a 5- or 6-membered ring. ), NR c (R c represents a hydrogen atom or a substituent), O, S, SiR d R e (R d and R e each independently represents a hydrogen atom or a substituent, and R d and R e may be combined to form a 5- or 6-membered ring), and A 1 to A 4 each independently represent CR f (R f represents a hydrogen atom or a substituent, And the two CR f may be combined to form a 5- or 6-membered ring.), N represents, R 1 to R 8 each independently represents a hydrogen atom or a substituent, and R 1 Two adjacent ones of -R 8 may jointly form a 5- or 6-membered ring.
- Substituent group A An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon
- the compound represented by the general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescent element.
- an organic layer which may contain the compound represented by the general formula (1) a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block Layer (a hole block layer, an electron block layer, etc.), etc., preferably a light emitting layer, an exciton block layer, a charge block layer, an electron transport layer, an electron injection layer, more preferably A light emitting layer, an exciton blocking layer, a charge blocking layer, or an electron transporting layer, more preferably a light emitting layer.
- the light emitting layer in the organic electroluminescent device of the present invention may be composed only of the light emitting material, or may be a mixed layer of a host material and the light emitting material.
- the kind of the light emitting material may be one kind or two kinds or more.
- the host material is preferably a charge transport material.
- the host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed.
- the light emitting layer may include a material that does not have charge transporting properties and does not emit light.
- Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
- R S1 to R S5 When a plurality of R S1 to R S5 are present, they may be bonded to each other to form a ring, and may further have a substituent Z.
- a represents an integer of 0 to 4, and when a plurality of R S1 are present, they may be the same or different and may be bonded to each other to form a ring.
- the organic electroluminescent element of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and contains at least one compound represented by the following general formula (P) in the organic layer. Is preferable from the viewpoints of element efficiency and driving voltage. Below, general formula (P) is demonstrated.
- the compound represented by the general formula (P) is described in WO2003 / 060956, WO2004 / 080975, JP2008-133277, WO2004 / 063159, JP2009-108066, and the like. It can be synthesized by the method. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.
- the compound represented by the general formula (P) is preferably contained in the organic layer between the light emitting layer and the cathode, but may be contained in a layer adjacent to the cathode. More preferred.
- the compound represented by the general formula (P) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.
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Abstract
Description
また、特許文献2にも、ピレン骨格に5員環が縮環した類似化合物を用いた有機電界発光素子が記載されている。特許文献2においても、良好な発光効率で青色発光を実現し、高輝度を達成したことが記載されている。
さらに、ピレン骨格を有する化合物を用いた有機電界発光素子については、これら以外にも幾つかの開発成果が報告されている(例えば特許文献3~7参照)。 For example, Patent Document 1 describes an organic electroluminescent device using a wide range of condensed ring compounds. Among them, examples of organic electroluminescence devices using a compound in which a 5-membered ring is condensed to a pyrene skeleton are mentioned, and blue light emission was realized with good luminous efficiency and a long life was achieved. Are listed.
In addition to these, several development results have been reported for organic electroluminescent devices using a compound having a pyrene skeleton (see, for example, Patent Documents 3 to 7).
該基板上に配置され、陽極及び陰極を含む一対の電極と、
該電極間に配置された有機層とを有し、
前記有機層が、下記一般式(1)で表される化合物を含有することを特徴とする有機電界発光素子。
[2] 前記一般式(1)において、XはCRaRb(Ra、Rbはそれぞれ独立に水素原子または置換基を表し、RaとRbは共同して5または6員環を形成していてもよい。)であることを特徴とする[1]に記載の有機電界発光素子。
[3] 前記一般式(1)において、R1~R8の少なくとも一つがフッ素原子、アルキル基、シリル基のいずれかを有する置換基であることを特徴とする[1]または[2]に記載の有機電界発光素子。
[4] 前記一般式(1)において、A1~A4が全てCRf(Rfは水素原子または置換基を表し、隣り合う2つのCRfは共同して5または6員環を形成していてもよい。)であることを特徴とする[1]~[3]のいずれか一項に記載の有機電界発光素子。
[5] 前記一般式(1)で表される化合物が下記一般式(2)で表されることを特徴とする[1]に記載の有機電界発光素子。
[6] 前記一般式(2)において、R10が-NRc'Rd'基(Rc'、Rd'はそれぞれ独立に置換基)であることを特徴とする[5]に記載の有機電界発光素子。
[7] 前記一般式(1)で表される化合物が下記一般式(3)で表されることを特徴とする[1]に記載の有機電界発光素子。
[8] 前記一般式(1)で表される化合物が下記一般式(4)で表されることを特徴とする[1]に記載の有機電界発光素子。
[9] 前記一般式(1)で表される化合物が下記一般式(5)で表されることを特徴とする[1]に記載の有機電界発光素子。
[10] 前記一般式(1)で表される化合物の分子量が800以下であることを特徴とする[1]~[9]のいずれか一項に記載の有機電界発光素子。
[11] 前記一般式(1)で表される化合物を含む有機層が発光層であることを特徴とする[1]~[10]のいずれか一項に記載の有機電界発光素子。
[12] 前記一般式(1)で表される化合物が発光材料であることを特徴とする[1]~[11]のいずれか一項に記載の有機電界発光素子。
[13] 前記有機層の少なくとも一層に下記一般式(An-1)で表される化合物を含むことを特徴とする[1]~[12]のいずれかに記載の有機電界発光素子。
[14] 前記一般式(An-1)で表される化合物が、下記(An-2)で表される化合物であることを特徴とする[13]に記載の有機電界発光素子。
[15] 前記一般式(An-1)で表される化合物を含む少なくとも一層の有機層が前記発光層であることを特徴とする[13]または[14]に記載の有機電界発光素子。
[16] [1]~[15]のいずれか一項に記載の有機電界発光素子は、前記有機層の少なくとも一層に下記一般式(P)で表される化合物を含むことが好ましい。
[17] [16]に記載の有機電界発光素子は、前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-1)で表される置換基を有する化合物であることが好ましい。
[18] [16]に記載の有機電界発光素子は、前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-2)で表される置換基を有する化合物であることが好ましい。
[19] [16]に記載の有機電界発光素子は、前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-3)で表される置換基を有する化合物であることが好ましい。
[20] [16]に記載の有機電界発光素子は、前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-4)で表される置換基を有する化合物であることが好ましい。
[21] [16]に記載の有機電界発光素子は、前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-5)で表される置換基を有する化合物であることが好ましい。
[22] 前記一般式(1)で表される化合物を含む有機層が真空蒸着プロセスにて形成されてなることを特徴とする[1]~[21]のいずれか一項に記載の有機電界発光素子。
[23] 前記一般式(1)で表される化合物を含む有機層が湿式プロセスにて形成されてなることを特徴とする[1]~[21]のいずれか一項に記載の有機電界発光素子。 [1] a substrate;
A pair of electrodes disposed on the substrate, including an anode and a cathode;
An organic layer disposed between the electrodes,
The said organic layer contains the compound represented by following General formula (1), The organic electroluminescent element characterized by the above-mentioned.
[2] In the general formula (1), X represents CR a R b (R a , R b each independently represents a hydrogen atom or a substituent, and R a and R b together form a 5- or 6-membered ring. The organic electroluminescence device according to [1], which may be formed.
[3] In the above general formula (1), at least one of R 1 to R 8 is a substituent having any one of a fluorine atom, an alkyl group, and a silyl group. The organic electroluminescent element as described.
[4] In the general formula (1), A 1 to A 4 are all CR f (R f represents a hydrogen atom or a substituent, and two adjacent CR f together form a 5- or 6-membered ring. The organic electroluminescent element according to any one of [1] to [3], which is characterized in that:
[5] The organic electroluminescent element as described in [1], wherein the compound represented by the general formula (1) is represented by the following general formula (2).
[6] As described in [5], in the general formula (2), R 10 is a —NR c ′ R d ′ group (R c ′ and R d ′ are each independently a substituent). Organic electroluminescent device.
[7] The organic electroluminescent element as described in [1], wherein the compound represented by the general formula (1) is represented by the following general formula (3).
[8] The organic electroluminescent element as described in [1], wherein the compound represented by the general formula (1) is represented by the following general formula (4).
[9] The organic electroluminescent element as described in [1], wherein the compound represented by the general formula (1) is represented by the following general formula (5).
[10] The organic electroluminescent element as described in any one of [1] to [9], wherein the molecular weight of the compound represented by the general formula (1) is 800 or less.
[11] The organic electroluminescent element as described in any one of [1] to [10], wherein the organic layer containing the compound represented by the general formula (1) is a light emitting layer.
[12] The organic electroluminescent element as described in any one of [1] to [11], wherein the compound represented by the general formula (1) is a luminescent material.
[13] The organic electroluminescent element as described in any one of [1] to [12], wherein a compound represented by the following general formula (An-1) is contained in at least one layer of the organic layer.
[14] The organic electroluminescent element as described in [13], wherein the compound represented by the general formula (An-1) is a compound represented by the following (An-2).
[15] The organic electroluminescent element as described in [13] or [14], wherein at least one organic layer containing the compound represented by the general formula (An-1) is the light emitting layer.
[16] The organic electroluminescent element according to any one of [1] to [15] preferably includes a compound represented by the following general formula (P) in at least one layer of the organic layer.
[17] In the organic electroluminescent device according to [16], the compound represented by the general formula (P) is a substituent represented by the general formula (P-1) as at least one of R P. It is preferable that it is a compound which has this.
[18] In the organic electroluminescent device according to [16], the compound represented by the general formula (P) is a substituent represented by the general formula (P-2) as at least one of R P. It is preferable that it is a compound which has this.
[19] In the organic electroluminescent device according to [16], the compound represented by the general formula (P) is a substituent represented by the general formula (P-3) as at least one of R P. It is preferable that it is a compound which has this.
[20] In the organic electroluminescent device according to [16], the compound represented by the general formula (P) is a substituent represented by the general formula (P-4) as at least one of R P. It is preferable that it is a compound which has this.
[21] In the organic electroluminescent device according to [16], the compound represented by the general formula (P) is a substituent represented by the general formula (P-5) as at least one of R P. It is preferable that it is a compound which has this.
[22] The organic electric field according to any one of [1] to [21], wherein the organic layer containing the compound represented by the general formula (1) is formed by a vacuum deposition process. Light emitting element.
[23] The organic electroluminescence according to any one of [1] to [21], wherein the organic layer containing the compound represented by the general formula (1) is formed by a wet process. element.
[25] 下記一般式(1)で表される化合物。
[25] A compound represented by the following general formula (1).
本発明の有機電界発光素子は、有機電界発光素子を構成する有機層が下記一般式(1)で表される化合物を含有することを特徴とする。
The organic electroluminescent element of the present invention is characterized in that the organic layer constituting the organic electroluminescent element contains a compound represented by the following general formula (1).
しかしながら、ピレン系化合物はモノマー発光より長波長な会合発光(エキシマー発光)を生じやすいという性質を有しているため、単にピレン環とアリール置換基を縮環するだけでは会合発光を生じて色純度低下を招いてしまいやすい。本発明の一般式(1)で表される化合物は、ピレン環平面から立体的に張り出したRa、Rbがピレン環同士の会合を効果的に抑制するものと考えられる。このため、単にピレン環とアリール置換基を縮環しただけでRa、Rbを有さない従来の縮環化合物と比べて、本発明の一般式(1)で表される化合物はピレン環のより中心部に置換基が張り出す構造を有するため、会合抑制効果が高いものと考えられる。縮環部分のRa、Rb以外にR1~R8の少なくとも一つがフッ素原子、アルキル基、シリル基のいずれかを有する置換基である場合はさらに会合が起こりにくい。 The sharpening of the emission spectrum of the compound represented by the general formula (1) is not bound by any theory, but the structure becomes rigid by condensing the pyrene ring and the aryl substituent. In addition, it is considered that the structural change between the ground state and the excited state is further reduced.
However, since pyrene compounds have the property of easily producing associated light emission (excimer light emission) with a wavelength longer than that of monomer light emission, simply by condensing a pyrene ring and an aryl substituent, the associated light emission is produced, resulting in color purity. It tends to cause a decline. In the compound represented by the general formula (1) of the present invention, it is considered that R a and R b sterically protruding from the plane of the pyrene ring effectively suppress the association of the pyrene rings. For this reason, the compound represented by the general formula (1) of the present invention is a pyrene ring as compared with a conventional condensed ring compound which does not have R a and R b simply by condensing a pyrene ring and an aryl substituent. Since it has a structure in which a substituent protrudes from the center of the structure, it is considered that the effect of suppressing association is high. When at least one of R 1 to R 8 is a substituent having any of a fluorine atom, an alkyl group, and a silyl group in addition to R a and R b of the condensed ring portion, association is less likely to occur.
本発明において、前記一般式(1)の説明における水素原子は同位体(重水素原子等)も含み、またさらに置換基を構成する原子は、その同位体も含んでいることを表す。
本発明において、「置換基」というとき、その置換基はさらに置換されていてもよい。例えば、本発明で「アルキル基」と言う時、フッ素原子で置換されたアルキル基(例えばトリフルオロメチル基)やアリール基で置換されたアルキル基(例えばトリフェニルメチル基)なども含むが、「炭素数1~6のアルキル基」と言うとき、置換されたものも含めた全ての基として炭素数が1~6であることを示す。 Hereinafter, the compound represented by the general formula (1) will be described in detail.
In the present invention, the hydrogen atom in the description of the general formula (1) includes an isotope (deuterium atom and the like), and the atoms constituting the substituent further include the isotope.
In the present invention, when the term “substituent” is used, the substituent may be further substituted. For example, the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group). When the term “alkyl group having 1 to 6 carbon atoms” is used, it means that all groups including substituted ones have 1 to 6 carbon atoms.
CRaRbは、その炭素原子が一般式(1)で表される化合物の環の構成原子となり、RaとRbはその炭素原子に結合する水素原子または置換基を表す。RaとRbは同一であっても異なっていてもよい。また、RaとRbは共同して5または6員環を形成していてもよい。NRcは、その窒素原子が一般式(1)で表される化合物の環の構成原子となり、Rcはその窒素原子に結合する水素原子または置換基を表す。SiRdReはその珪素原子が一般式(1)で表される化合物の環の構成原子となり、RdとReはその珪素原子に結合する水素原子または置換基を表す。RdとReは同一であっても異なっていてもよい。また、RdとReは共同して5または6員環を形成していてもよい。
一般式(1)におけるXとしては、CRaRbがより好ましい。 In the general formula (1), X represents any of CR a R b , NR c , O, S, SiR d R e .
CR a R b represents a constituent atom of the ring of the compound represented by the general formula (1), and R a and R b represent a hydrogen atom or a substituent bonded to the carbon atom. R a and R b may be the same or different. R a and R b may jointly form a 5- or 6-membered ring. In NR c , the nitrogen atom is a constituent atom of the ring of the compound represented by the general formula (1), and R c represents a hydrogen atom or a substituent bonded to the nitrogen atom. SiR d R e is a constituent atom of the ring of the compound represented by the general formula (1), and R d and R e represent a hydrogen atom or a substituent bonded to the silicon atom. R d and Re may be the same or different. R d and Re may jointly form a 5- or 6-membered ring.
As X in the general formula (1), CR a R b is more preferable.
《置換基群A》
アルキル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~10であり、例えばメチル、エチル、イソプロピル、t-ブチル、n-オクチル、n-デシル、n-ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシルなどが挙げられる。)、アルケニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばビニル、アリル、2-ブテニル、3-ペンテニルなどが挙げられる。)、アルキニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばプロパルギル、3-ペンチニルなどが挙げられる。)、アリール基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニル、p-メチルフェニル、ナフチル、アントラニルなどが挙げられる。)、アミノ基(好ましくは炭素数0~30、より好ましくは炭素数0~20、特に好ましくは炭素数0~10であり、例えばアミノ、メチルアミノ、ジメチルアミノ、ジエチルアミノ、ジベンジルアミノ、ジフェニルアミノ、ジトリルアミノなどが挙げられる。)、アルコキシ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~10であり、例えばメトキシ、エトキシ、ブトキシ、2-エチルヘキシロキシなどが挙げられる。)、アリールオキシ基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニルオキシ、1-ナフチルオキシ、2-ナフチルオキシなどが挙げられる。)、ヘテロ環オキシ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばピリジルオキシ、ピラジルオキシ、ピリミジルオキシ、キノリルオキシなどが挙げられる。)、アシル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~12であり、例えばアセチル、ベンゾイル、ホルミル、ピバロイルなどが挙げられる。)、アルコキシカルボニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~12であり、例えばメトキシカルボニル、エトキシカルボニルなどが挙げられる。)、アリールオキシカルボニル基(好ましくは炭素数7~30、より好ましくは炭素数7~20、特に好ましくは炭素数7~12であり、例えばフェニルオキシカルボニルなどが挙げられる。)、アシルオキシ基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばアセトキシ、ベンゾイルオキシなどが挙げられる。)、アシルアミノ基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばアセチルアミノ、ベンゾイルアミノなどが挙げられる。)、アルコキシカルボニルアミノ基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~12であり、例えばメトキシカルボニルアミノなどが挙げられる。)、アリールオキシカルボニルアミノ基(好ましくは炭素数7~30、より好ましくは炭素数7~20、特に好ましくは炭素数7~12であり、例えばフェニルオキシカルボニルアミノなどが挙げられる。)、スルホニルアミノ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメタンスルホニルアミノ、ベンゼンスルホニルアミノなどが挙げられる。)、スルファモイル基(好ましくは炭素数0~30、より好ましくは炭素数0~20、特に好ましくは炭素数0~12であり、例えばスルファモイル、メチルスルファモイル、ジメチルスルファモイル、フェニルスルファモイルなどが挙げられる。)、カルバモイル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばカルバモイル、メチルカルバモイル、ジエチルカルバモイル、フェニルカルバモイルなどが挙げられる。)、アルキルチオ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメチルチオ、エチルチオなどが挙げられる。)、アリールチオ基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニルチオなどが挙げられる。)、ヘテロ環チオ基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばピリジルチオ、2-ベンズイミゾリルチオ、2-ベンズオキサゾリルチオ、2-ベンズチアゾリルチオなどが挙げられる。)、スルホニル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメシル、トシルなどが挙げられる。)、スルフィニル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばメタンスルフィニル、ベンゼンスルフィニルなどが挙げられる。)、ウレイド基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばウレイド、メチルウレイド、フェニルウレイドなどが挙げられる。)、リン酸アミド基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~12であり、例えばジエチルリン酸アミド、フェニルリン酸アミドなどが挙げられる。)、ヒドロキシ基、メルカプト基、ハロゲン原子(例えばフッ素原子、塩素原子、臭素原子、ヨウ素原子)、シアノ基、スルホ基、カルボキシル基、ニトロ基、ヒドロキサム酸基、スルフィノ基、ヒドラジノ基、イミノ基、ヘテロ環基(芳香族ヘテロ環基も包含し、好ましくは炭素数1~30、より好ましくは炭素数1~12であり、ヘテロ原子としては、例えば窒素原子、酸素原子、硫黄原子、リン原子、ケイ素原子、セレン原子、テルル原子であり、具体的にはピリジル、ピラジニル、ピリミジル、ピリダジニル、ピロリル、ピラゾリル、トリアゾリル、イミダゾリル、オキサゾリル、チアゾリル、イソキサゾリル、イソチアゾリル、キノリル、フリル、チエニル、セレノフェニル、テルロフェニル、ピペリジル、ピペリジノ、モルホリノ、ピロリジル、ピロリジノ、ベンゾオキサゾリル、ベンゾイミダゾリル、ベンゾチアゾリル、カルバゾリル基、アゼピニル基、シロリル基などが挙げられる。)、シリル基(好ましくは炭素数3~40、より好ましくは炭素数3~30、特に好ましくは炭素数3~24であり、例えばトリメチルシリル、トリフェニルシリルなどが挙げられる。)、シリルオキシ基(好ましくは炭素数3~40、より好ましくは炭素数3~30、特に好ましくは炭素数3~24であり、例えばトリメチルシリルオキシ、トリフェニルシリルオキシなどが挙げられる。)、ホスホリル基(例えばジフェニルホスホリル基、ジメチルホスホリル基などが挙げられる。)が挙げられる。これらの置換基は更に置換されてもよく、更なる置換基としては、以上に説明した置換基群Aから選択される基を挙げることができる。また、置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Aから選択される基を挙げることができる。また、置換基に置換した置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Aから選択される基を挙げることができる。 Examples of the substituents (substituents on carbon atoms and substituents on silicon atoms) that R a , R b , R d , and R e can take include the following substituent group A. R a, R b, R d , substituent R e may take is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a fluorine atom.
<< Substituent group A >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), amino groups (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms). Particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms, Preferably it has 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. Xy, 1-naphthyloxy, 2-naphthyloxy, etc.), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms). , Benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl, ethoxy Carbonyl, etc.), an aryloxycarbonyl group (preferably having a carbon number) The number of carbon atoms is 7 to 30, more preferably 7 to 20, and particularly preferably 7 to 12, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy, etc.), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and alkoxycarbonylamino groups (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), an aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), carbamoyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.), an arylthio group (preferably 6 to 30 carbon atoms). More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio), a sulfonyl group (preferably having a carbon number) 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl). Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenyl phosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( An aromatic heterocyclic group is also included, preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like. A silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). A aryloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.
《置換基群B》
アルキル基(好ましくは炭素数1~30、より好ましくは炭素数1~20、特に好ましくは炭素数1~10であり、例えばメチル、エチル、イソプロピル、t-ブチル、n-オクチル、n-デシル、n-ヘキサデシル、シクロプロピル、シクロペンチル、シクロヘキシルなどが挙げられる。)、アルケニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばビニル、アリル、2-ブテニル、3-ペンテニルなどが挙げられる。)、アルキニル基(好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばプロパルギル、3-ペンチニルなどが挙げられる。)、アリール基(好ましくは炭素数6~30、より好ましくは炭素数6~20、特に好ましくは炭素数6~12であり、例えばフェニル、p-メチルフェニル、ナフチル、アントラニルなどが挙げられる。)、シアノ基、ヘテロ環基(芳香族ヘテロ環基も包含し、好ましくは炭素数1~30、より好ましくは炭素数1~12であり、ヘテロ原子としては、例えば窒素原子、酸素原子、硫黄原子、リン原子、ケイ素原子、セレン原子、テルル原子であり、具体的にはピリジル、ピラジニル、ピリミジル、ピリダジニル、ピロリル、ピラゾリル、トリアゾリル、イミダゾリル、オキサゾリル、チアゾリル、イソキサゾリル、イソチアゾリル、キノリル、フリル、チエニル、セレノフェニル、テルロフェニル、ピペリジル、ピペリジノ、モルホリノ、ピロリジル、ピロリジノ、ベンゾオキサゾリル、ベンゾイミダゾリル、ベンゾチアゾリル、カルバゾリル基、アゼピニル基、シロリル基などが挙げられる。)これらの置換基は更に置換されてもよく、更なる置換基としては、前記置換基群Bから選択される基を挙げることができる。また、置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Bから選択される基を挙げることができる。また、置換基に置換した置換基に置換した置換基は更に置換されてもよく、さらなる置換基としては、以上に説明した置換基群Bから選択される基を挙げることができる。 Examples of the substituent (substituent on the nitrogen atom) that R c can take include the following substituent group B. The substituent that R c can take is preferably an alkyl group, a perfluoroalkyl group, an aryl group, or a fluorine atom.
<< Substituent group B >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably 6 to 6 carbon atoms). 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthranyl, etc.), cyano group, heterocyclic group (including aromatic heterocyclic group, preferably carbon The hetero atom is, for example, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, or a tellurium atom, specifically, pyridyl. , Pyrazinyl, pyrimidyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, Benzimidazolyl, Nzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and examples of further substituents include groups selected from the aforementioned substituent group B. . Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group B described above.
CRfは、その炭素原子が一般式(1)で表される化合物の環の構成原子となり、Rfはその炭素原子に結合する水素原子または置換基を表す。Rfがとりうる置換基としては、上記の置換基群Aを挙げることができる。Rfがとりうる置換基は、フッ素原子、アルキル基、シリル基、アリール基、シアノ基、アミノ基のいずれかを有する置換基であることが好ましい。具体的には、アルキル基、ペルフルオロアルキル基、アリール基、アルコキシ基、フッ素原子、シアノ基、ジアリールアミノ基、トリアルキルシリル基を挙げることができる。
一般式(1)におけるA1~A4のうちの2つ以上がCRfを表すとき、そのうちの隣り合う2つのCRfは共同して5または6員環を形成していてもよい。形成される5または6員環は、シクロアルケニル環、ベンゼン環、ヘテロアリール環のいずれであってもよい。ヘテロアリール環としては、環を構成する原子の中に、窒素原子、酸素原子および硫黄原子からなる群より選択されるヘテロ原子を1~3個含むものを挙げることができる。具体的には、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環、イミダゾール環、オキサゾール環、チアゾール環、ピラゾール環、チオフェン環、フラン環などを例示することができる。形成される5または6員環は置換基を有していてもよく、炭素原子上の置換基としては上記の置換基群Aが挙げられ、窒素原子上の置換基については上記の置換基群Bが挙げられる。 In the general formula (1), A 1 to A 4 each independently represent either CR f or N. For example, a case where A 1 to A 4 are all CR f can be cited as a preferred example.
CR f represents a constituent atom of the ring of the compound represented by the general formula (1), and R f represents a hydrogen atom or a substituent bonded to the carbon atom. Examples of the substituent that R f can take include the substituent group A described above. The substituent that R f can take is preferably a substituent having any of a fluorine atom, an alkyl group, a silyl group, an aryl group, a cyano group, and an amino group. Specific examples include alkyl groups, perfluoroalkyl groups, aryl groups, alkoxy groups, fluorine atoms, cyano groups, diarylamino groups, and trialkylsilyl groups.
When two or more of A 1 to A 4 in the general formula (1) represent CR f , the two adjacent CR f may jointly form a 5- or 6-membered ring. The formed 5- or 6-membered ring may be a cycloalkenyl ring, a benzene ring, or a heteroaryl ring. Examples of the heteroaryl ring include those having 1 to 3 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom among the atoms constituting the ring. Specific examples include a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, a pyrazole ring, a thiophene ring, and a furan ring. The formed 5- or 6-membered ring may have a substituent, and examples of the substituent on the carbon atom include the above-described substituent group A, and the substituent on the nitrogen atom includes the above-described substituent group B is mentioned.
一般式(2)において、R1~R12はそれぞれ独立に水素原子または置換基を表し、Ra、Rbはそれぞれ独立に水素原子または置換基を表し、R9~R12のうちのいずれか2つで共同して置換または無置換のベンゼン環を形成している。
一般式(2)におけるR1~R8の説明と好ましい範囲は、一般式(1)におけるR1~R8の説明と好ましい範囲と同じである。一般式(2)におけるRaおよびRbの説明と好ましい範囲は、一般式(1)の説明中におけるRaおよびRbの説明と好ましい範囲と同じである。一般式(2)におけるR9~R12が水素原子または置換基を表すとき、それらの説明と好ましい範囲は一般式(1)におけるR1~R8の説明と好ましい範囲と同じである。一般式(2)のR9~R12のいずれか2つは共同して置換または無置換のベンゼン環を形成している。R9とR10が共同して置換または無置換のベンゼン環を形成している場合と、R10とR11が共同して置換または無置換のベンゼン環を形成している場合を好ましい例として挙げることができる。これらのベンゼン環は、さらに置換基群Aの置換基などで置換されていてもよく、またさらにベンゼン環等が縮合していてもよい。
一般式(2)において、R10が-NRc'Rd'基(Rc'、Rd'はそれぞれ独立に置換基)であることが、発光波長および発光効率の観点から好ましい。Rc'およびRd'はそれぞれ独立にアルキル基、アリール基またはヘテロアリール基を表すことが好ましく、互いに結合して環を形成していてもよい。Rc'およびRd'はそれぞれ独立にアリール基またはヘテロアリール基であることがより好ましく、アリール基であることが特に好ましく、炭素数6~10のアリール基であることがより特に好ましく、フェニル基または2-ナフチル基であることがよりさらに特に好ましい。Rc'およびRd'はさらなる置換基を有していてもよく、さらなる置換基としては、アルキル基、アリール基またはフッ素原子が好ましく、炭素数1~5のアルキル基、フェニル基またはフッ素原子がより好ましく、メチル基が特に好ましい。Rc'およびRd'がさらなる置換基を有する場合のさらなる置換基の個数は、Rc'およびRd'あたり、1~3個であることが好ましく、1または2個であることがより好ましく、1個であることが特に好ましい。 In the general formula (2), R 1 to R 12 each independently represents a hydrogen atom or a substituent, and two adjacent ones of R 1 to R 8 jointly form a 5- or 6-membered ring. Also good. Any two of R 9 to R 12 together form a substituted or unsubstituted benzene ring. R a and R b each independently represent a hydrogen atom or a substituent, and R a and R b may jointly form a 5- or 6-membered ring.
In the general formula (2), R 1 to R 12 each independently represents a hydrogen atom or a substituent, R a and R b each independently represent a hydrogen atom or a substituent, and any one of R 9 to R 12 These two together form a substituted or unsubstituted benzene ring.
The explanation and preferred range of R 1 to R 8 in the general formula (2) are the same as the explanation and preferred range of R 1 to R 8 in the general formula (1). Description and the preferred range of R a and R b in the general formula (2) are the same as the preferable range as described in R a and R b in the description of general formula (1). When R 9 to R 12 in the general formula (2) represent a hydrogen atom or a substituent, their explanation and preferred range are the same as those of R 1 to R 8 in the general formula (1). Any two of R 9 to R 12 in the general formula (2) jointly form a substituted or unsubstituted benzene ring. Preferred examples include a case where R 9 and R 10 jointly form a substituted or unsubstituted benzene ring and a case where R 10 and R 11 jointly form a substituted or unsubstituted benzene ring. Can be mentioned. These benzene rings may be further substituted with a substituent of the substituent group A or the like, and further a benzene ring or the like may be condensed.
In the general formula (2), R 10 is preferably a —NR c ′ R d ′ group (R c ′ and R d ′ are each independently a substituent) from the viewpoint of emission wavelength and emission efficiency. R c ′ and R d ′ each preferably independently represent an alkyl group, an aryl group or a heteroaryl group, and may be bonded to each other to form a ring. R c ′ and R d ′ are preferably each independently an aryl group or a heteroaryl group, more preferably an aryl group, and particularly preferably an aryl group having 6 to 10 carbon atoms. It is even more particularly preferred that it is a group or a 2-naphthyl group. R c ′ and R d ′ may have a further substituent, and as the further substituent, an alkyl group, an aryl group or a fluorine atom is preferable, and an alkyl group having 1 to 5 carbon atoms, a phenyl group or a fluorine atom Are more preferable, and a methyl group is particularly preferable. When R c ′ and R d ′ have a further substituent, the number of further substituents is preferably 1 to 3 and more preferably 1 or 2 per R c ′ and R d ′. One is particularly preferable.
一般式(3)におけるR1、R4~R16の説明と好ましい範囲は、一般式(1)におけるR1~R8の説明と好ましい範囲と同じである。一般式(3)におけるRa、Rb、Ra' 、Rb'の説明と好ましい範囲は、一般式(1)の説明中におけるRaおよびRbの説明と好ましい範囲と同じである。 In the general formula (3), R 1 and R 4 to R 16 each independently represent a hydrogen atom or a substituent, and adjacent two of R 1 and R 4 to R 16 are 5 or 6-membered together. A ring may be formed. R a , R b , R a ′ and R b ′ each independently represent a hydrogen atom or a substituent, and R a and R b may jointly form a 5- or 6-membered ring, and R a ′ And R b ′ may together form a 5- or 6-membered ring.
The explanation and preferred range of R 1 , R 4 to R 16 in the general formula (3) are the same as the explanation and preferred range of R 1 to R 8 in the general formula (1). The explanation and preferred range of R a , R b , R a ′ and R b ′ in the general formula (3) are the same as the explanation and preferred range of R a and R b in the explanation of the general formula (1).
一般式(4)におけるR1~R3、R6~R12、R17~R20の説明と好ましい範囲は、一般式(1)におけるR1~R8の説明と好ましい範囲と同じである。一般式(4)におけるRa、Rb、Ra" 、Rb"の説明と好ましい範囲は、一般式(1)の説明中におけるRaおよびRbの説明と好ましい範囲と同じである。 In the general formula (4), R 1 to R 3 , R 6 to R 12 , and R 17 to R 20 each independently represent a hydrogen atom or a substituent, and R 1 to R 3 , R 6 to R 12 , R 17 Two adjacent ones of -R 20 may jointly form a 5- or 6-membered ring. R a , R b , R a ″ and R b ″ each independently represent a hydrogen atom or a substituent, and R a and R b may jointly form a 5- or 6-membered ring, and R a ″ And R b ″ may together form a 5- or 6-membered ring.
Descriptions and preferred ranges of R 1 to R 3 , R 6 to R 12 , R 17 to R 20 in the general formula (4) are the same as those of R 1 to R 8 in the general formula (1). . The explanation and preferred range of R a , R b , R a ″ and R b ″ in the general formula (4) are the same as the explanation and preferred range of R a and R b in the explanation of the general formula (1).
一般式(5)におけるR3~R12およびR21~R24の説明と好ましい範囲は、一般式(1)におけるR1~R8の説明と好ましい範囲と同じである。一般式(4)におけるRa、Rb、Ra'''およびRb'''の説明と好ましい範囲は、一般式(1)の説明中におけるRaおよびRbの説明と好ましい範囲と同じである。 The compound represented by the general formula (1) is preferably represented by the following general formula (5).
The explanation and preferred range of R 3 to R 12 and R 21 to R 24 in the general formula (5) are the same as the explanation and preferred range of R 1 to R 8 in the general formula (1). The explanation and preferred range of R a , R b , R a ′ ″ and R b ′ ″ in the general formula (4) are the same as the explanation and preferred range of R a and R b in the explanation of the general formula (1). The same.
合成後、カラムクロマトグラフィー、再結晶等による精製を行った後、昇華精製により精製することが好ましい。昇華精製により、有機不純物を分離できるだけでなく、無機塩や残留溶媒等を効果的に取り除くことができる。 The synthetic intermediate A having various substituents can be synthesized by combining known reactions. For example, compounds having substituents at R 1 and R 6 can be synthesized by the methods described in JP2008-101182A, JP2008-127291A, and the like. The compounds having substituents on R 2 , R 5 , and R 7 are described in WO2005 / 108348, JP2006-176494, JP2009-4351, JP2009-35516, and the like. Can be synthesized. Compounds having substituents at R 3 , R 4 and R 8 can be synthesized by the method described in JP-A-2008-127291. For the reaction conditions of Steps 1 to 4 (4 ′), WO2010 / 012328 can be referred to. R 1 to R 8 may be introduced at any stage of the synthesis intermediates A to E (E ′).
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.
本発明の有機電界発光素子は、基板と、該基板上に配置され、陽極及び陰極を含む一対の電極と、該電極間に配置された有機層とを有し、前記有機層が一般式(1)で表される化合物を含むことを特徴とする。
本発明の有機電界発光素子の構成は、特に制限されることはない。図1に、本発明の有機電界発光素子の構成の一例を示す。図1の有機電界発光素子10は、基板2上に、一対の電極(陽極3と陰極9)の間に有機層を有する。
有機電界発光素子の素子構成、基板、陰極及び陽極については、例えば、特開2008-270736号公報に詳述されており、該公報に記載の事項を本発明に適用することができる。
以下、本発明の有機電界発光素子の好ましい態様について、基板、電極、有機層、保護層、封止容器、駆動方法、発光波長、用途の順で詳細に説明する。 [Organic electroluminescence device]
The organic electroluminescent element of the present invention comprises a substrate, a pair of electrodes including an anode and a cathode disposed on the substrate, and an organic layer disposed between the electrodes. It includes a compound represented by 1).
The structure of the organic electroluminescent element of the present invention is not particularly limited. In FIG. 1, an example of a structure of the organic electroluminescent element of this invention is shown. 1 has an organic layer on a
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
Hereinafter, the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board | substrate, an electrode, an organic layer, a protective layer, a sealing container, a drive method, light emission wavelength, and a use.
本発明の有機電界発光素子は、基板を有する。
本発明で使用する基板としては、有機層から発せられる光を散乱又は減衰させない基板であることが好ましい。有機材料の場合には、耐熱性、寸法安定性、耐溶剤性、電気絶縁性、及び加工性に優れていることが好ましい。 <Board>
The organic electroluminescent element of the present invention has a substrate.
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.
本発明の有機電界発光素子は、前記基板上に配置され、陽極及び陰極を含む一対の電極を有する。
発光素子の性質上、一対の電極である陽極及び陰極のうち少なくとも一方の電極は、透明若しくは半透明であることが好ましい。 <Electrode>
The organic electroluminescent element of the present invention is disposed on the substrate and has a pair of electrodes including an anode and a cathode.
In view of the properties of the light-emitting element, at least one of the pair of electrodes, the anode and the cathode, is preferably transparent or translucent.
陽極は、通常、有機層に正孔を供給する電極としての機能を有していればよく、その形状、構造、大きさ等については特に制限はなく、発光素子の用途、目的に応じて、公知の電極材料の中から適宜選択することができる。前述のごとく、陽極は、通常透明陽極として設けられる。 (anode)
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.
陰極は、通常、有機層に電子を注入する電極としての機能を有していればよく、その形状、構造、大きさ等については特に制限はなく、発光素子の用途、目的に応じて、公知の電極材料の中から適宜選択することができる。 (cathode)
The cathode usually has a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., and it is known depending on the use and purpose of the light-emitting element. The electrode material can be selected as appropriate.
本発明の有機電界発光素子は、前記電極間に配置された有機層を有し、前記有機層が一般式(1)で表される化合物を含むことを特徴とする。
前記有機層は、特に制限はなく、有機電界発光素子の用途、目的に応じて適宜選択することができるが、前記透明電極上に又は前記半透明電極上に形成されるのが好ましい。この場合、有機層は、前記透明電極又は前記半透明電極上の全面又は一面に形成される。
有機層の形状、大きさ、及び厚み等については、特に制限はなく、目的に応じて適宜選択することができる。
以下、本発明の有機電界発光素子における、有機層の構成、有機層の形成方法、有機層を構成する各層の好ましい態様および各層に使用される材料について順に説明する。 <Organic layer>
The organic electroluminescent element of the present invention has an organic layer disposed between the electrodes, and the organic layer contains a compound represented by the general formula (1).
There is no restriction | limiting in particular in the said organic layer, Although it can select suitably according to the use and objective of an organic electroluminescent element, It is preferable to form on the said transparent electrode or the said semi-transparent electrode. In this case, the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
There is no restriction | limiting in particular about the shape of a organic layer, a magnitude | size, thickness, etc., According to the objective, it can select suitably.
Hereinafter, in the organic electroluminescent element of the present invention, the configuration of the organic layer, the method for forming the organic layer, preferred embodiments of the layers constituting the organic layer, and materials used for the layers will be described in order.
本発明の有機電界発光素子では、前記有機層が、電荷輸送層を含むことが好ましい。前記電荷輸送層とは、有機電界発光素子に電圧を印加した際に電荷移動が起こる層をいう。具体的には正孔注入層、正孔輸送層、電子ブロック層、発光層、正孔ブロック層、電子輸送層又は電子注入層が挙げられる。前記電荷輸送層が正孔注入層、正孔輸送層、電子ブロック層又は発光層であれば、低コストかつ高効率な有機電界発光素子の製造が可能となる。 (Organic layer structure)
In the organic electroluminescent element of the present invention, the organic layer preferably includes a charge transport layer. The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
前記一般式(1)で表される化合物を含有してもよい有機層としては、発光層、正孔注入層、正孔輸送層、電子輸送層、電子注入層、励起子ブロック層、電荷ブロック層(正孔ブロック層、電子ブロック層など)などを挙げることができ、好ましくは、発光層、励起子ブロック層、電荷ブロック層、電子輸送層、電子注入層のいずれかであり、より好ましくは発光層、励起子ブロック層、電荷ブロック層、又は電子輸送層であり、更に好ましくは発光層である。 The compound represented by the general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescent element.
As an organic layer which may contain the compound represented by the general formula (1), a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block Layer (a hole block layer, an electron block layer, etc.), etc., preferably a light emitting layer, an exciton block layer, a charge block layer, an electron transport layer, an electron injection layer, more preferably A light emitting layer, an exciton blocking layer, a charge blocking layer, or an electron transporting layer, more preferably a light emitting layer.
本発明の有機電界発光素子において、各有機層は、蒸着法やスパッタ法等の乾式製膜法、転写法、印刷法、スピンコート法、バーコート法等の湿式製膜法(溶液塗布法)のいずれによっても好適に形成することができる。
本発明の有機電界発光素子は、前記一対の電極間に配置された有機層が、少なくとも一層の前記一般式(1)で表される化合物を含む組成物の蒸着により形成されていることが好ましい。 (Formation method of organic layer)
In the organic electroluminescence device of the present invention, each organic layer is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
In the organic electroluminescent element of the present invention, it is preferable that the organic layer disposed between the pair of electrodes is formed by vapor deposition of a composition containing at least one compound represented by the general formula (1). .
発光層は、電界印加時に、陽極、正孔注入層又は正孔輸送層から正孔を受け取り、陰極、電子注入層又は電子輸送層から電子を受け取り、正孔と電子の再結合の場を提供して発光させる機能を有する層である。但し、本発明における前記発光層は、このようなメカニズムによる発光に必ずしも限定されるものではない。 (Light emitting layer)
The light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light. However, the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism.
本発明の有機電界発光素子では、前記一般式(1)で表される化合物を発光材料とすることが好ましいが、その場合であっても前記一般式(1)で表される化合物とは別の発光材料を組み合わせて用いることが可能である。また、本発明の有機電界発光素子において、前記一般式(1)で表される化合物を発光層のホスト材料として使用する場合や、発光層以外の有機層に用いる場合にも、前記一般式(1)で表される化合物とは別の発光材料を発光層に用いる。
本発明において用いることができる発光材料は、燐光発光材料、蛍光発光材料等のいずれであってもよい。また、本発明における発光層は、色純度を向上させたり、発光波長領域を広げたりするために、2種類以上の発光材料を含有することができる。 (Luminescent material)
In the organic electroluminescent element of the present invention, the compound represented by the general formula (1) is preferably used as a luminescent material, but even in that case, it is different from the compound represented by the general formula (1). These light emitting materials can be used in combination. Moreover, in the organic electroluminescent element of the present invention, when the compound represented by the general formula (1) is used as a host material of the light emitting layer, or when used in an organic layer other than the light emitting layer, the general formula ( A light emitting material different from the compound represented by 1) is used for the light emitting layer.
The light emitting material that can be used in the present invention may be any of a phosphorescent light emitting material, a fluorescent light emitting material, and the like. In addition, the light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve color purity or broaden the light emission wavelength region.
本発明に使用できる燐光発光材料としては、例えば、米国特許第6303238号明細書、米国特許第6097147号明細書、WO00/57676号公報、WO00/70655号公報、WO01/08230号公報、WO01/39234号公報、WO01/41512号公報、WO02/02714号公報、WO02/15645号公報、WO02/44189号公報、WO05/19373号公報、特開2001-247859号公報、特開2002-302671号公報、特開2002-117978号公報、特開2003-133074号公報、特開2002-235076号公報、特開2003-123982号公報、特開2002-170684号公報、欧州特許公開第1211257号公報、特開2002-226495号公報、特開2002-234894号公報、特開2001-247859号公報、特開2001-298470号公報、特開2002-173674号公報、特開2002-203678号公報、特開2002-203679号公報、特開2004-357791号公報、特開2006-256999号公報、特開2007-19462号公報、特開2007-84635号公報、特開2007-96259号公報等の特許文献に記載の燐光発光化合物などが挙げられ、中でも、更に好ましい発光材料としては、Ir錯体、Pt錯体、Cu錯体、Re錯体、W錯体、Rh錯体、Ru錯体、Pd錯体、Os錯体、Eu錯体、Tb錯体、Gd錯体、Dy錯体、及びCe錯体等の燐光発光性金属錯体化合物が挙げられる。特に好ましくは、Ir錯体、Pt錯体、又はRe錯体であり、中でも金属-炭素結合、金属-窒素結合、金属-酸素結合、金属-硫黄結合の少なくとも一つの配位様式を含むIr錯体、Pt錯体、又はRe錯体が好ましい。更に、発光効率、駆動耐久性、色度等の観点で、Ir錯体、Pt錯体が特に好ましく、Ir錯体が最も好ましい。 Examples of the fluorescent light-emitting material and the phosphorescent light-emitting material that can be used in the organic electroluminescent element of the present invention include, for example, paragraphs [0100] to [0164] of JP-A-2008-270736 and JP-A-2007-266458. Paragraph numbers [0088] to [0090] are described in detail, and the matters described in these publications can be applied to the present invention.
Examples of phosphorescent materials that can be used in the present invention include US Pat. No. 6,303,238, US Pat. No. 6,097,147, WO 00/57676, WO 00/70655, WO 01/08230, WO 01/39234. No., WO01 / 41512, WO02 / 02714, WO02 / 15645, WO02 / 44189, WO05 / 19373, JP2001-247859, JP2002-302671, JP 2002-117978, JP 2003-133074, JP 2002-235076, JP 2003-123982, JP 2002-170684, European Patent Publication No. 121112257, JP 2002 -22649 JP, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-173684, JP 2002-203678, JP 2002-203679. Phosphorescent light emitting compounds described in patent documents such as JP-A No. 2004-357791, JP-A No. 2006-256999, JP-A No. 2007-19462, JP-A No. 2007-84635, JP-A No. 2007-96259, etc. Among them, more preferable light-emitting materials include Ir complex, Pt complex, Cu complex, Re complex, W complex, Rh complex, Ru complex, Pd complex, Os complex, Eu complex, Tb complex, Gd complex, Examples thereof include phosphorescent metal complex compounds such as Dy complexes and Ce complexes. Particularly preferred is an Ir complex, a Pt complex, or a Re complex, among which an Ir complex or a Pt complex containing at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, and a metal-sulfur bond. Or Re complexes are preferred. Furthermore, from the viewpoints of luminous efficiency, driving durability, chromaticity and the like, an Ir complex and a Pt complex are particularly preferable, and an Ir complex is most preferable.
本発明の有機電界発光素子における発光層は、発光材料のみで構成されていてもよく、ホスト材料と発光材料の混合層とした構成でもよい。発光材料の種類は一種であっても二種以上であっても良い。ホスト材料は電荷輸送材料であることが好ましい。ホスト材料は一種であっても二種以上であってもよく、例えば、電子輸送性のホスト材料と正孔輸送性のホスト材料を混合した構成が挙げられる。更に、発光層中に電荷輸送性を有さず、発光しない材料を含んでいてもよい。
また、発光層は一層であっても二層以上の多層であってもよく、それぞれの層に同じ発光材料やホスト材料を含んでもよいし、層毎に異なる材料を含んでもよい。発光層が複数の場合、それぞれの発光層が異なる発光色で発光してもよい。 In addition, the compounds described in [0082] of JP2010-111620A can also be used as the light emitting material.
The light emitting layer in the organic electroluminescent element of the present invention may be composed only of a light emitting material, or may be a mixed layer of a host material and a light emitting material. The kind of the light emitting material may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.
ホスト材料とは、発光層において主に電荷の注入、輸送を担う化合物であり、また、それ自体は実質的に発光しない化合物のことである。ここで「実質的に発光しない」とは、該実質的に発光しない化合物からの発光量が好ましくは素子全体での全発光量の5%以下であり、より好ましくは3%以下であり、更に好ましくは1%以下であることを言う。 (Host material)
The host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
ピロール、インドール、カルバゾール、アザインドール、アザカルバゾール、トリアゾール、オキサゾール、オキサジアゾール、ピラゾール、イミダゾール、チオフェン、ベンゾチオフェン、ジベンゾチオフェン、フラン、ベンゾフラン、ジベンゾフラン、ポリアリールアルカン、ピラゾリン、ピラゾロン、フェニレンジアミン、アリールアミン、アミノ置換カルコン、スチリルアントラセン、フルオレノン、ヒドラゾン、スチルベン、シラザン、芳香族第三級アミン化合物、スチリルアミン化合物、ポルフィリン系化合物、縮環芳香族炭化水素化合物(フルオレン、ナフタレン、フェナントレン、トリフェニレン等)、ポリシラン系化合物、ポリ(N-ビニルカルバゾール)、アニリン系共重合体、チオフェンオリゴマー、ポリチオフェン等の導電性高分子オリゴマー、有機シラン、カーボン膜、ピリジン、ピリミジン、トリアジン、イミダゾール、ピラゾール、トリアゾ-ル、オキサゾ-ル、オキサジアゾ-ル、フルオレノン、アントラキノジメタン、アントロン、ジフェニルキノン、チオピランジオキシド、カルボジイミド、フルオレニリデンメタン、ジスチリルピラジン、フッ素置換芳香族化合物、ナフタレンペリレン等の複素環テトラカルボン酸無水物、フタロシアニン、8-キノリノ-ル誘導体の金属錯体やメタルフタロシアニン、ベンゾオキサゾ-ルやベンゾチアゾ-ルを配位子とする金属錯体に代表される各種金属錯体及びそれらの誘導体(置換基や縮環を有していてもよい)等を挙げることができる。その他に、特開2010-111620の[0081]や[0083]に記載される化合物を用いることもできる。
これらのうち、カルバゾール、ジベンゾチオフェン、ジベンゾフラン、アリールアミン、縮環芳香族炭化水素化合物、金属錯体が好ましく、縮環芳香族炭化水素化合物が安定であるために特に好ましい。縮環芳香族炭化水素化合物としてはナフタレン系化合物、アントラセン系化合物、フェナントレン系化合物、トリフェニレン系化合物、ピレン系化合物が好ましく、アントラセン系化合物、ピレン系化合物がより好ましく、アントラセン系化合物が特に好ましい。アントラセン系化合物としては、WO2010/134350号公報の[0033]~[0064]に記載のものが特に好ましく、例えば後掲の化合物H-1やH-2を挙げることができる。 Examples of the host material that can be used in the organic electroluminescence device of the present invention include the following compounds.
Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amines, amino-substituted chalcones, styrylanthracenes, fluorenones, hydrazones, stilbenes, silazanes, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, condensed aromatic hydrocarbon compounds (fluorene, naphthalene, phenanthrene, triphenylene, etc.) , Polysilane compound, poly (N-vinylcarbazole), aniline copolymer, thiophene oligomer, polythiophene Conductive polymer oligomer, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone, thiopyrandi Oxides, carbodiimides, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, metal complexes of phthalocyanines and 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles, Examples thereof include various metal complexes represented by metal complexes having benzothiazol as a ligand and derivatives thereof (which may have a substituent or a condensed ring). In addition, compounds described in [0081] and [0083] of JP2010-111620A can also be used.
Of these, carbazole, dibenzothiophene, dibenzofuran, arylamine, a condensed ring aromatic hydrocarbon compound, and a metal complex are preferable, and a condensed ring aromatic hydrocarbon compound is particularly preferable because it is stable. As the condensed aromatic hydrocarbon compound, naphthalene compounds, anthracene compounds, phenanthrene compounds, triphenylene compounds and pyrene compounds are preferable, anthracene compounds and pyrene compounds are more preferable, and anthracene compounds are particularly preferable. As the anthracene compounds, those described in [0033] to [0064] of WO2010 / 134350 are particularly preferable, and examples thereof include compounds H-1 and H-2 described later.
Ar1およびAr2が表すヘテロアリール基としては、環員数5~20のヘテロアリール基であることが好ましく、環員数5~13のヘテロアリール基であることがより好ましい。Ar1およびAr2が表すヘテロアリール基に含まれるヘテロ原子としては、窒素原子、酸素原子および硫黄原子が好ましく、窒素原子がより好ましい。Ar1およびAr2が表すヘテロアリール基中に含まれるヘテロ原子の数は、1~3個であることが好ましく、1または2個であることがより好ましく、1個であることが特に好ましい。Ar1およびAr2が表すヘテロアリール基としては、ピリジル基、カルバゾリル基、ジベンゾフリル基、ジベンゾチオフェニル基であることが特に好ましい。
Ar1およびAr2として好ましくはフェニル基、ナフチル基、ピリジル基、カルバゾリル基、ジベンゾフリル基、ジベンゾチオフェニル基、およびこれらを組み合わせてなる基である。Ar1およびAr2はその中でもフェニル基またはナフチル基であることがより好ましく、Ar1およびAr2のうち少なくとも一方が置換または無置換のフェニル基であることが特に好ましい。
Ar1、Ar2はさらに置換基を有していてもよく、該置換基としてはアリール基、ヘテロアリール基、フッ素原子、アルキル基(炭素数1~4であることが好ましい)、アルケニル基、シリル基、シアノ基を挙げることができる。 In general formula (An-1), the aryl group represented by Ar 1 and Ar 2 is preferably an aryl group having 6 to 36 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, An aryl group having 6 to 14 carbon atoms is particularly preferable, and a phenyl group or a naphthyl group is particularly preferable.
The heteroaryl group represented by Ar 1 and Ar 2 is preferably a heteroaryl group having 5 to 20 ring members, and more preferably a heteroaryl group having 5 to 13 ring members. As a hetero atom contained in the heteroaryl group represented by Ar 1 and Ar 2 , a nitrogen atom, an oxygen atom and a sulfur atom are preferable, and a nitrogen atom is more preferable. The number of heteroatoms contained in the heteroaryl group represented by Ar 1 and Ar 2 is preferably 1 to 3, more preferably 1 or 2, and particularly preferably 1. The heteroaryl group represented by Ar 1 and Ar 2 is particularly preferably a pyridyl group, a carbazolyl group, a dibenzofuryl group, or a dibenzothiophenyl group.
Ar 1 and Ar 2 are preferably a phenyl group, a naphthyl group, a pyridyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothiophenyl group, and a group formed by combining these. Ar 1 and Ar 2 are more preferably a phenyl group or a naphthyl group, and at least one of Ar 1 and Ar 2 is particularly preferably a substituted or unsubstituted phenyl group.
Ar 1, Ar 2 may further have a substituent, Examples of the optionally substituted aryl group, a heteroaryl group, a fluorine atom, (preferably a number of 1 to 4 carbon atoms) alkyl group, an alkenyl group, A silyl group and a cyano group can be mentioned.
一般式(An-1)中、R301~R308はさらに置換基を有していてもよく、該置換基としてはアリール基、ヘテロアリール基およびアルキル基を挙げることができ、アリール基およびヘテロアリール基が好ましく、炭素数6~18のアリール基がより好ましい。
一般式(An-1)中、R301~R308に含まれる置換基の数は0~4個であることが好ましく、0または2個であることがより好ましく、0または1個であることが特に好ましく、0個であることがより特に好ましい。
一般式(An-1)中、R301~R308に含まれる置換基の位置はR302、R303、R306またはR307であることが好ましく、R302およびR303のいずれか一方またはR306およびR307のいずれか一方であることがより好ましい。
一般式(An-1)中、R301とR302、R302とR303、R303とR304、R305とR306、R306とR307及びR307とR308は互いに結合して環を形成してもよいが、これらは互いに結合して環を形成しないことが好ましい。 In the general formula (An-1), examples of the substituent represented by R 301 to R 308 include an aryl group, a heteroaryl group, a fluorine atom, an alkyl group, a silyl group, a cyano group, and a group formed by combining these. Preferably a phenyl group, a naphthyl group, a pyridyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothiophenyl group, a fluorine atom, an alkyl group, a silyl group, a cyano group, and a combination thereof, and a phenyl group And more preferably a naphthyl group and an alkyl group having 1 to 5 carbon atoms (particularly preferably a tert-butyl group).
In general formula (An-1), R 301 to R 308 may further have a substituent, and examples of the substituent include an aryl group, a heteroaryl group, and an alkyl group. An aryl group is preferable, and an aryl group having 6 to 18 carbon atoms is more preferable.
In general formula (An-1), the number of substituents contained in R 301 to R 308 is preferably 0 to 4, more preferably 0 or 2, and 0 or 1 Is particularly preferable, and 0 is more particularly preferable.
In the general formula (An-1), the position of the substituent contained in R 301 to R 308 is preferably R 302 , R 303 , R 306 or R 307 , and either one of R 302 and R 303 or R More preferably, either one of 306 and R307 is used.
In general formula (An-1), R 301 and R 302 , R 302 and R 303 , R 303 and R 304 , R 305 and R 306 , R 306 and R 307, and R 307 and R 308 are bonded to each other to form a ring. However, it is preferable that they are not bonded to each other to form a ring.
一般式(An-1)中、R309~R318はさらに置換基を有していてもよく、該置換基としてはアリール基、アルキル基、フッ素原子などを挙げることができ、該置換基どうしが互いに結合して環を形成してもよい。
一般式(An-1)中、R309~R318に含まれる置換基の数は0~4個であることが好ましく、0または2個であることがより好ましく、0または1個であることが特に好ましく、0個であることがより特に好ましい。
一般式(An-1)中、R309~R318に含まれる置換基の位置に特に制限はないが、置換基を有する場合はR311およびR316のうち少なくとも一方に有することが好ましい。
一般式(An-1)中、R309とR310、R310とR311、R311とR312、R312とR313、R314とR315、R315とR316、R316とR317及びR317とR318は互いに結合して環を形成してもよく、形成される環は5または6員環であることが好ましく、5員環であることがより好ましい。 Examples of the substituent represented by R 309 to R 318 in the general formula (An-2) include an aryl group, a heteroaryl group, a fluorine atom, an alkyl group, a silyl group, a cyano group, and a group formed by combining these. , An aryl group having 6 to 18 carbon atoms, a heteroaryl group having 5 to 20 ring members, a fluorine atom, an alkyl group, an alkenyl group, a silyl group, a cyano group, and a combination thereof, more preferably a phenyl group , A naphthyl group, a pyridyl group, a carbazolyl group, a dibenzofuryl group, a dibenzothiophenyl group, a fluorine atom, an alkyl group, an alkenyl group, a silyl group, a cyano group, and a combination thereof, particularly preferably a phenyl group, A naphthyl group and a carbazolyl group;
In general formula (An-1), R 309 to R 318 may further have a substituent, and examples of the substituent include an aryl group, an alkyl group, a fluorine atom, and the like. May combine with each other to form a ring.
In general formula (An-1), the number of substituents contained in R 309 to R 318 is preferably 0 to 4, more preferably 0 or 2, and 0 or 1 Is particularly preferable, and 0 is particularly preferable.
In the general formula (An-1), the position of the substituent contained in R 309 to R 318 is not particularly limited, but when it has a substituent, it is preferably contained in at least one of R 311 and R 316 .
In general formula (An-1), R 309 and R 310 , R 310 and R 311 , R 311 and R 312 , R 312 and R 313 , R 314 and R 315 , R 315 and R 316 , R 316 and R 317 R 317 and R 318 may combine with each other to form a ring, and the formed ring is preferably a 5- or 6-membered ring, and more preferably a 5-membered ring.
ホスト材料の膜状態でのS1が発光材料のS1より小さいと発光を消光してしまうためホスト材料には発光材料より大きなS1が求められる。また、ホスト材料のS1が発光材料より大きい場合でも、両者のS1差が小さい場合には一部、発光材料からホスト材料への逆エネルギー移動が起こるため、効率低下や色純度低下、耐久性低下の原因となる。従って、S1が十分に大きく、化学的安定性及びキャリア注入・輸送性の高いホスト材料が求められる。 In the light emitting layer, the singlet minimum excitation energy (S 1 energy) in the film state of the host material is preferably higher than the S 1 energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S 1 is greater than 0.1eV than S 1 of the light-emitting material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
The host material for S 1 in the film state of the host material will be quench S 1 is smaller than the light emission of the light emitting material larger S 1 is obtained from the luminescent material. Even if the S 1 of the host material is larger than the light emitting material, if the S 1 difference between the two is small, the reverse energy transfer from the light emitting material to the host material occurs in part, resulting in a decrease in efficiency, color purity, and durability. Cause deterioration of sex. Accordingly, there is a demand for a host material having a sufficiently large S 1 and high chemical stability and carrier injection / transport properties.
本発明の有機電界発光素子は、前記発光層以外のその他の層を有していてもよい。
前記有機層が有していてもよい前記発光層以外のその他の有機層として、正孔注入層、正孔輸送層、ブロック層(正孔ブロック層、励起子ブロック層など)、電子輸送層などが挙げられる。前記具体的な層構成として、下記が挙げられるが本発明はこれらの構成に限定されるものではない。
・陽極/正孔輸送層/発光層/電子輸送層/陰極、
・陽極/正孔輸送層/発光層/ブロック層/電子輸送層/陰極、
・陽極/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/陰極、
・陽極/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/陰極、
・陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極、
・陽極/正孔注入層/正孔輸送層/発光層/ブロック層/電子輸送層/電子注入層/陰極、
・陽極/正孔注入層/正孔輸送層/ブロック層/発光層/ブロック層/電子輸送層/電子注入層/陰極。
本発明の有機電界発光素子は、(A)前記陽極と前記発光層との間に好ましく配置される有機層を少なくとも一層含むことが好ましい。前記(A)前記陽極と前記発光層との間に好ましく配置される有機層としては、陽極側から正孔注入層、正孔輸送層、電子ブロック層を挙げることができる。
本発明の有機電界発光素子は、(B)前記陰極と前記発光層との間に好ましく配置される有機層少なくとも一層含むことが好ましい。前記(B)前記陰極と前記発光層との間に好ましく配置される有機層としては、陰極側から電子注入層、電子輸送層、正孔ブロック層を挙げることができる。
具体的には、本発明の有機電界発光素子の好ましい態様の一例は、図1に記載される態様であり、前記有機層として、陽極側3から正孔注入層4、正孔輸送層5、発光層6、正孔ブロック層7及び電子輸送層8がこの順に積層されている態様である。
以下、これら本発明の有機電界発光素子が有していてもよい前記発光層以外のその他の層について、説明する。 (Other layers)
The organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / block layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The organic electroluminescent element of the present invention preferably includes (A) at least one organic layer preferably disposed between the anode and the light emitting layer. Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
The organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer. Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
Specifically, an example of a preferred embodiment of the organic electroluminescent element of the present invention is the embodiment described in FIG. 1, and as the organic layer, a
Hereinafter, other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.
まず、(A)前記陽極と前記発光層との間に好ましく配置される有機層について説明する。 (A) Organic layer preferably disposed between the anode and the light emitting layer First, (A) the organic layer preferably disposed between the anode and the light emitting layer will be described.
正孔注入層、正孔輸送層は、陽極又は陽極側から正孔を受け取り陰極側に輸送する機能を有する層である。 (A-1) Hole injection layer, hole transport layer The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
前記一般式(Sa-1)中、Xは、置換または無置換の炭素数1~30のアルキレン基、置換または無置換の炭素数2~30のアルケニレン基、置換または無置換の炭素数6~30のアリーレン基、置換または無置換の炭素数2~30のヘテロアリーレン基、置換または無置換の炭素数2~30の複素環基、あるいは、これらの基を組み合わせてなる基を表す。Xとして好ましくは、置換または無置換の炭素数6~30のアリーレン基であり、より好ましくは、置換または無置換のフェニレン、置換または無置換のビフェニレン、および、置換または無置換のナフチレンであり、さらに好ましくは置換または無置換のビフェニレンである。
RS1、RS2、RS3は、各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数1~30のアルコキシ基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数6~30のアリールオキシ基、置換または無置換の炭素数2~30の複素環、置換または無置換の炭素数5~30の縮合多環基、ヒドロキシ基、シアノ基、あるいは、置換または無置換のアミノ基を表す。隣接するRS1、RS2、RS3同士が互いに結合し、飽和炭素環または不飽和炭素環を形成してもよい。前記飽和炭素環または当該不飽和炭素環の例としては、ナフタレン、アズレン、アントラセン、フルオレン、フェナレンなどがある。RS1、RS2、RS3として好ましくは、水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数5~30の縮合多環基、および、シアノ基であり、より好ましくは水素原子である。
ArS1、ArS2は、各々独立に、置換または無置換の炭素数6~30のアリール基、あるいは、置換または無置換の炭素数2~30のヘテロアリール基を表す。ArS1、ArS2として好ましくは、置換または無置換のフェニル基である。 The general formula (Sa-1) will be described.
In the general formula (Sa-1), X represents a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 6 to 6 carbon atoms. It represents a 30 arylene group, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a group formed by combining these groups. X is preferably a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, and a substituted or unsubstituted naphthylene. More preferred is substituted or unsubstituted biphenylene.
R S1 , R S2 and R S3 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon An aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms, a substituted or unsubstituted condensed group having 5 to 30 carbon atoms A cyclic group, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group is represented. Adjacent R S1 , R S2 and R S3 may be bonded to each other to form a saturated or unsaturated carbocycle. Examples of the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene. R S1 , R S2 and R S3 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon number. A condensed polycyclic group of 5 to 30 and a cyano group, more preferably a hydrogen atom.
Ar S1 and Ar S2 each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Ar S1 and Ar S2 are preferably a substituted or unsubstituted phenyl group.
前記一般式(Sb-1)中、RS4、RS5、RS6およびRS7は、各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数1~30のアルコキシ基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数6~30のアリールオキシ基、置換または無置換の炭素数2~30の複素環、または置換または無置換の炭素数5~30の縮合多環基、ヒドロキシ基、シアノ基、あるいは、置換または無置換のアミノ基を表す。隣接するRS4、RS5、RS6およびRS7同士が互いに結合し、飽和炭素環または不飽和炭素環を形成してもよい。前記飽和炭素環または当該不飽和炭素環の例としては、ナフタレン、アズレン、アントラセン、フルオレン、フェナレンなどがある。RS4、RS5、RS6およびRS7として好ましくは、水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数5~30の縮合多環基、および、シアノ基であり、より好ましくは水素原子である。
ArS3は、置換または無置換の炭素数6~30のアリール基、あるいは、置換または無置換の炭素数2~30のヘテロアリール基を表す。ArS3として好ましくは、置換または無置換のフェニル基である。 Next, the general formula (Sb-1) will be described.
In the general formula (Sb-1), R S4 , R S5 , R S6 and R S7 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number. An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms, Or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms, a hydroxy group, a cyano group, or a substituted or unsubstituted amino group; Adjacent R S4 , R S5 , R S6 and R S7 may be bonded to each other to form a saturated or unsaturated carbocycle. Examples of the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene. R S4 , R S5 , R S6 and R S7 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A condensed polycyclic group having 5 to 30 carbon atoms and a cyano group, more preferably a hydrogen atom.
Ar S3 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Ar S3 is preferably a substituted or unsubstituted phenyl group.
前記一般式(Sc-1)中、RS8およびRS9は各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数2~30の複素環基、あるいは、置換または無置換の炭素数5~30の縮合多環基を表す。RS8およびRS9として好ましくは、置換または無置換の炭素数1~30のアルキル基、および、置換または無置換の炭素数6~30のアリール基であり、より好ましくは、メチル基およびフェニル基である。RS10は置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数2~30の複素環基、あるいは、置換または無置換の炭素数5~30の縮合多環基を表す。RS10として好ましくは置換または無置換の炭素数6~30のアリール基であり、より好ましくはフェニル基である。RS11およびRS12は、各々独立に水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数1~30のアルコキシ基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数6~30のアリールオキシ基、置換または無置換の炭素数2~30の複素環、置換または無置換の炭素数5~30の縮合多環基、ヒドロキシ基、シアノ基、あるいは、置換または無置換のアミノ基を表す。隣接するRS11およびRS12同士が互いに結合し、飽和炭素環または不飽和炭素環を形成してもよい。前記飽和炭素環または当該不飽和炭素環の例としては、ナフタレン、アズレン、アントラセン、フルオレン、フェナレンなどがある。RS11およびRS12として好ましくは、水素原子、置換または無置換の炭素数1~30のアルキル基、置換または無置換の炭素数6~30のアリール基、置換または無置換の炭素数5~30の縮合多環基、および、シアノ基であり、より好ましくは水素原子である。ArS4は、置換または無置換の炭素数6~30のアリール基、あるいは、置換または無置換の炭素数2~30のヘテロアリール基を表す。YS1、YS2は置換または無置換の炭素数1~30のアルキレン、あるいは、置換または無置換の炭素数6~30のアリーレンを表す。YS1、YS2として好ましくは、置換または無置換の炭素数6~30のアリーレンであり、より好ましくは置換または無置換のフェニレンである。nは0~5の整数であり、好ましくは0~3、より好ましくは0~2、さらに好ましくは0である。mは0~5の整数であり、好ましくは0~3、より好ましくは0~2、さらに好ましくは1である。 Next, the general formula (Sc-1) will be described.
In the general formula (Sc-1), R S8 and R S9 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, It represents a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted condensed polycyclic group having 5 to 30 carbon atoms. R S8 and R S9 are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably a methyl group or a phenyl group. It is. R S10 represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, It represents an unsubstituted condensed polycyclic group having 5 to 30 carbon atoms. R S10 is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and more preferably a phenyl group. R S11 and R S12 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 6 to 30 aryl groups, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic rings having 2 to 30 carbon atoms, substituted or unsubstituted condensed polycyclic groups having 5 to 30 carbon atoms, It represents a hydroxy group, a cyano group, or a substituted or unsubstituted amino group. Adjacent R S11 and R S12 may be bonded to each other to form a saturated or unsaturated carbocycle. Examples of the saturated carbocycle or the unsaturated carbocycle include naphthalene, azulene, anthracene, fluorene, and phenalene. R S11 and R S12 are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon group having 5 to 30 carbon atoms. A condensed polycyclic group and a cyano group, and more preferably a hydrogen atom. Ar S4 represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. Y S1 and Y S2 represent substituted or unsubstituted alkylene having 1 to 30 carbon atoms, or substituted or unsubstituted arylene having 6 to 30 carbon atoms. Y S1 and Y S2 are preferably substituted or unsubstituted arylene having 6 to 30 carbon atoms, and more preferably substituted or unsubstituted phenylene. n is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still more preferably 0. m is an integer of 0 to 5, preferably 0 to 3, more preferably 0 to 2, and still more preferably 1.
前記一般式(Sa-1)、(Sb-1)または(Sc-1)で表される化合物は、添加する有機層の全質量に対して70~100質量%含まれることが好ましく、85~100質量%含まれることがより好ましい。 In the light emitting device of the present invention, the compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) is contained in an organic layer between the light emitting layer and the anode. Among them, it is more preferable that it be contained in a layer on the anode side adjacent to the light emitting layer, and a hole transport material contained in the hole transport layer is particularly preferable.
The compound represented by the general formula (Sa-1), (Sb-1) or (Sc-1) is preferably contained in an amount of 70 to 100% by mass based on the total mass of the organic layer to be added, It is more preferable that 100 mass% is contained.
本発明の有機電界発光素子は、前記(A)陽極と前記発光層との間に好ましく配置される有機層に特に好ましく用いられる材料として、少なくとも一種の下記一般式(M-3)で表される化合物を挙げることができる。 [Compound represented by formula (M-3)]
The organic electroluminescent device of the present invention is represented by at least one of the following general formula (M-3) as a material particularly preferably used for the organic layer preferably disposed between the (A) anode and the light emitting layer. Can be mentioned.
前記一般式(M-3)で表される化合物が含有される、発光層と陽極の間の発光層に隣接する有機層は、電子ブロック層又は正孔輸送層であることがより好ましい。 The compound represented by the general formula (M-3) is more preferably contained in an organic layer adjacent to the light emitting layer between the light emitting layer and the anode, but its use is not limited, and the organic layer It may be further contained in any of the layers. As the introduction layer of the compound represented by the general formula (M-3), a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a charge blocking layer, or a plurality of layers are included. Can be contained.
The organic layer adjacent to the light emitting layer between the light emitting layer and the anode and containing the compound represented by the general formula (M-3) is more preferably an electron blocking layer or a hole transporting layer.
aは0~4の整数を表し、複数のRS1が存在するとき、それらは同一でも異なっていてもよく、互いに結合して環を形成してもよい。b~eはそれぞれ独立に0~5の整数を表し、それぞれ複数のRS2~RS5が存在するとき、それらは同一でも異なっていてもよく、任意の2つが結合し環を形成してもよい。
qは1~5の整数であり、qが2以上のとき複数のRS1は同一でも異なっていてもよく、互いに結合して環を形成していてもよい。 In the general formula (M-3), R S1 to R S5 are each independently an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO 2 R, — C (O) R, —NR 2 , —NO 2 , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent Z. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group. When a plurality of R S1 to R S5 are present, they may be bonded to each other to form a ring, and may further have a substituent Z.
a represents an integer of 0 to 4, and when a plurality of R S1 are present, they may be the same or different and may be bonded to each other to form a ring. b to e each independently represent an integer of 0 to 5, and when there are a plurality of R S2 to R S5 , respectively, they may be the same or different, and any two may be bonded to form a ring. Good.
q is an integer of 1 to 5, and when q is 2 or more, a plurality of R S1 may be the same or different, and may be bonded to each other to form a ring.
シクロアルキル基としては、置換基を有していてもよく、飽和であっても不飽和であってもよく、置換してもよい基としては、前述の置換基Zを挙げることができる。RS1~RS5で表されるシクロアルキル基として、好ましくは環員数4~7のシクロアルキル基であり、より好ましくは総炭素原子数5~6のシクロアルキル基であり、例えばシクロペンチル基、シクロヘキシル基等が挙げられる。
RS1~RS5で表されるアルケニル基としては好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばビニル、アリル、1-プロペニル、1-イソプロペニル、1-ブテニル、2-ブテニル、3-ペンテニルなどが挙げられる。
RS1~RS5で表されるアルキニル基としては、好ましくは炭素数2~30、より好ましくは炭素数2~20、特に好ましくは炭素数2~10であり、例えばエチニル、プロパルギル、1-プロピニル、3-ペンチニルなどが挙げられる。 The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The alkyl group represented by R S1 to R S5 is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as a methyl group or an ethyl group. I-propyl group, cyclohexyl group, tert-butyl group and the like.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent Z. The cycloalkyl group represented by R S1 to R S5 is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total, such as a cyclopentyl group or cyclohexyl group. Groups and the like.
The alkenyl group represented by R S1 to R S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, 1-propenyl, Examples include 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
The alkynyl group represented by R S1 to R S5 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, ethynyl, propargyl, 1-propynyl , 3-pentynyl and the like.
また、前記一般式(M-3)で表される化合物を、複数の有機層に用いる場合はそれぞれの層において、上記の範囲で含有することが好ましい。 When the compound represented by the general formula (M-3) is used in the hole transport layer, the compound represented by the general formula (M-3) is preferably contained in an amount of 50 to 100% by mass. The content is preferably 80 to 100% by mass, and particularly preferably 95 to 100% by mass.
Further, when the compound represented by the general formula (M-3) is used in a plurality of organic layers, it is preferable that each layer contains the compound in the above range.
電子ブロック層は、陰極側から発光層に輸送された電子が、陽極側に通りぬけることを防止する機能を有する層である。本発明において、発光層と陽極側で隣接する有機層として、電子ブロック層を設けることができる。
電子ブロック層を構成する有機化合物の例としては、例えば前述の正孔輸送材料として挙げたものが適用できる。
電子ブロック層の厚さとしては、1nm~500nmであるのが好ましく、3nm~100nmであるのがより好ましく、5nm~50nmであるのが更に好ましい。
電子ブロック層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
電子ブロック層に用いる材料は、前記発光材料のS1エネルギーより高いことが色純度、発光効率、駆動耐久性の点で好ましい。電子ブロック層に用いる材料の膜状態でのS1が発光材料のS1より0.1eV以上大きいことが好ましく、0.2eV以上大きいことがより好ましく、0.3eV以上大きいことが更に好ましい。 (A-2) Electron Blocking Layer The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and even more preferably 5 nm to 50 nm.
The electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
The material used for the electron blocking layer is preferably higher than the S 1 energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S 1 is greater than 0.1eV than S 1 of the light-emitting material in the film state of the material used for the electron blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
次に、前記(B)陰極と前記発光層との間に好ましく配置される有機層について説明する。 (B) Organic layer preferably disposed between the cathode and the light emitting layer Next, the (B) organic layer preferably disposed between the cathode and the light emitting layer will be described.
電子注入層、電子輸送層は、陰極又は陰極側から電子を受け取り陽極側に輸送する機能を有する層である。これらの層に用いる電子注入材料、電子輸送材料は低分子化合物であっても高分子化合物であってもよい。
電子輸送材料としては、例えば前記一般式(1)で表される化合物を用いることができる。その他の電子輸送材料としては、ピリジン誘導体、キノリン誘導体、ピリミジン誘導体、ピラジン誘導体、フタラジン誘導体、フェナントロリン誘導体、トリアジン誘導体、トリアゾール誘導体、オキサゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ベンゾイミダゾール誘導体、イミダゾピリジン誘導体、フルオレノン誘導体、アントラキノジメタン誘導体、アントロン誘導体、ジフェニルキノン誘導体、チオピランジオキシド誘導体、カルボジイミド誘導体、フルオレニリデンメタン誘導体、ジスチリルピラジン誘導体、ナフタレン、ペリレン等の芳香環テトラカルボン酸無水物、フタロシアニン誘導体、8-キノリノール誘導体の金属錯体やメタルフタロシアニン、ベンゾオキサゾールやベンゾチアゾールを配位子とする金属錯体に代表される各種金属錯体、シロールに代表される有機シラン誘導体、ナフタレン、アントラセン、フェナントレン、トリフェニレン、ピレン等の縮環炭化水素化合物等をから選ばれることが好ましく、ピリジン誘導体、ベンゾイミダゾール誘導体、イミダゾピリジン誘導体、金属錯体、縮環炭化水素化合物のいずれかであることがより好ましい。 (B-1) Electron Injection Layer, Electron Transport Layer The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, for example, a compound represented by the general formula (1) can be used. Other electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, imidazopyridine derivatives. , Fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic tetracarboxylic anhydrides such as naphthalene and perylene, Metal complexes of phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles and benzothiazoles as ligands Various metal complexes typified by metal complexes, organosilane derivatives typified by siloles, condensed hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, triphenylene, pyrene, etc., are preferred, pyridine derivatives, benzimidazole derivatives , An imidazopyridine derivative, a metal complex, or a condensed ring hydrocarbon compound is more preferable.
電子輸送層の厚さとしては、1nm~500nmであるのが好ましく、5nm~200nmであるのがより好ましく、10nm~100nmであるのが更に好ましい。また、電子注入層の厚さとしては、0.1nm~200nmであるのが好ましく、0.2nm~100nmであるのがより好ましく、0.5nm~50nmであるのが更に好ましい。
電子注入層、電子輸送層は、上述した材料の1種又は2種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。 The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm. The thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
正孔ブロック層は、陽極側から発光層に輸送された正孔が、陰極側に通りぬけることを防止する機能を有する層である。本発明において、発光層と陰極側で隣接する有機層として、正孔ブロック層を設けることができる。
正孔ブロック層を構成する有機化合物の膜状態でのS1エネルギーは、発光層で生成する励起子のエネルギー移動を防止し、発光効率を低下させないために、発光材料のS1エネルギーよりも高いことが好ましい。
正孔ブロック層を構成する有機化合物の例としては、例えば前記一般式(1)で表される化合物を用いることができる。
前記一般式(1)で表される化合物以外の、正孔ブロック層を構成するその他の有機化合物の例としては、アルミニウム(III)ビス(2-メチル-8-キノリナト)4-フェニルフェノレート(Aluminum (III)bis(2-methyl-8-quinolinato)4-phenylphenolate(BAlqと略記する))等のアルミニウム錯体、トリアゾール誘導体、2,9-ジメチル-4,7-ジフェニル-1,10-フェナントロリン(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline(BCPと略記する))等のフェナントロリン誘導体、等が挙げられる。
正孔ブロック層の厚さとしては、1nm~500nmであるのが好ましく、3nm~100nmであるのがより好ましく、5nm~50nmであるのが更に好ましい。
正孔ブロック層は、上述した材料の一種又は二種以上からなる単層構造であってもよいし、同一組成又は異種組成の複数層からなる多層構造であってもよい。
正孔ブロック層に用いる材料は、前記発光材料のS1エネルギーより高いことが色純度、発光効率、駆動耐久性の点で好ましい。正孔ブロック層に用いる材料の膜状態でのS1が発光材料のS1より0.1eV以上大きいことが好ましく、0.2eV以上大きいことがより好ましく、0.3eV以上大きいことが更に好ましい。 (B-2) Hole blocking layer The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
The S 1 energy in the film state of the organic compound constituting the hole blocking layer is higher than the S 1 energy of the light emitting material in order to prevent the energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
As an example of the organic compound constituting the hole blocking layer, for example, a compound represented by the general formula (1) can be used.
Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as BAlq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, still more preferably 5 nm to 50 nm.
The hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
The material used for the hole blocking layer is preferably higher than the S 1 energy of the light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable S 1 is greater than 0.1eV than S 1 of the light-emitting material in the film state of the material used in the hole blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
本発明の有機電界発光素子は、前記(B)陰極と前記発光層との間に好ましく配置される有機層の材料に特に好ましく用いられる材料として、前記一般式(1)で表される化合物、下記一般式(P-1)で表される化合物および下記一般式(O-1)で表される化合物を挙げることができる。
以下、前記一般式(O-1)で表される化合物と、前記一般式(P-1)で表される化合物について説明する。 (B-3) Material particularly preferably used for the organic layer preferably disposed between the cathode and the light emitting layer The organic electroluminescent element of the present invention is preferably disposed between the (B) cathode and the light emitting layer. As a material particularly preferably used for the material of the organic layer, a compound represented by the general formula (1), a compound represented by the following general formula (P-1), and a compound represented by the following general formula (O-1) Can be mentioned.
Hereinafter, the compound represented by the general formula (O-1) and the compound represented by the general formula (P-1) will be described.
一般式(O-1)で表される化合物は、添加する有機層の全質量に対して70~100質量%含まれることが好ましく、85~100質量%含まれることがより好ましい。 In the organic electroluminescent device of the present invention, the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the cathode side layer adjacent to the light emitting layer is used. It is more preferable that it is contained.
The compound represented by the general formula (O-1) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.
RP1~RP5、R'P1~R'P3、R'P5、R"P3として、好ましくはアリール基、ヘテロアリール基のいずれかであり、より好ましくはアリール基であり、更に好ましくはフェニル基、ビフェニル基、ターフェニル基、ナフチル基のいずれかであり、最も好ましくはフェニル基である。
LP1~LP5として、好ましくは単結合、アリール環からなる二価の連結基のいずれかであり、より好ましくは単結合、フェニレン、ビフェニレン、ターフェニレン、ナフチレンのいずれかであり、更に好ましくは単結合、フェニレン、ナフチレンのいずれかである。 As R P , a preferable substituent other than the substituents represented by (P-1) to (P-5) is an aryl group, and more preferably any one of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group. And more preferably a naphthyl group.
R P1 to R P5 , R ′ P1 to R ′ P3 , R ′ P5 and R ″ P3 are preferably either an aryl group or a heteroaryl group, more preferably an aryl group, and still more preferably a phenyl group , A biphenyl group, a terphenyl group, or a naphthyl group, and most preferably a phenyl group.
L P1 to L P5 are preferably any of a single bond and a divalent linking group consisting of an aryl ring, more preferably a single bond, any of phenylene, biphenylene, terphenylene and naphthylene, and still more preferably It is either a single bond, phenylene, or naphthylene.
一般式(P)で表される化合物は、添加する有機層の全質量に対して70~100質量%含まれることが好ましく、85~100質量%含まれることがより好ましい。 In the organic electroluminescent element of the present invention, the compound represented by the general formula (P) is preferably contained in the organic layer between the light emitting layer and the cathode, but may be contained in a layer adjacent to the cathode. More preferred.
The compound represented by the general formula (P) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.
本発明において、有機電界素子全体は、保護層によって保護されていてもよい。
保護層については、特開2008-270736号公報の段落番号〔0169〕~〔0170〕に記載の事項を本発明に適用することができる。なお、保護層の材料は無機物であっても、有機物であってもよい。 <Protective layer>
In the present invention, the entire organic electric field element may be protected by a protective layer.
As for the protective layer, the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention. The material for the protective layer may be inorganic or organic.
本発明の有機電界発光素子は、封止容器を用いて素子全体を封止してもよい。
封止容器については、特開2008-270736号公報の段落番号〔0171〕に記載の事項を本発明に適用することができる。 <Sealing container>
The organic electroluminescent element of the present invention may be sealed entirely using a sealing container.
Regarding the sealing container, the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.
本発明の有機電界発光素子は、陽極と陰極との間に直流(必要に応じて交流成分を含んでもよい)電圧(通常2ボルト~15ボルト)、又は直流電流を印加することにより、発光を得ることができる。
本発明の有機電界発光素子の駆動方法については、特開平2-148687号、同6-301355号、同5-29080号、同7-134558号、同8-234685号、同8-241047号の各公報、特許第2784615号、米国特許5828429号、同6023308号の各明細書等に記載の駆動方法を適用することができる。 <Driving method>
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.
本発明の有機電界発光素子は、その発光波長に制限はない。例えば、光の三原色のうち、赤色の発光に用いても、緑色の発光に用いても、青色の発光に用いてもよい。その中でも、本発明の有機電界発光素子では、前記一般式(1)で表される化合物を発光材料として用いて発光させることが好ましく、特に青色発光させることが好ましい。 <Emission wavelength>
There is no restriction | limiting in the light emission wavelength of the organic electroluminescent element of this invention. For example, among the three primary colors of light, it may be used for red light emission, green light emission, or blue light emission. Among them, in the organic electroluminescent element of the present invention, it is preferable to emit light using the compound represented by the general formula (1) as a light emitting material, and it is particularly preferable to emit blue light.
本発明の有機電界発光素子は、表示素子、ディスプレイ、バックライト、電子写真、照明光源、記録光源、露光光源、読み取り光源、標識、看板、インテリア、又は光通信等に好適に利用できる。特に、発光装置、照明装置、表示装置等の発光輝度が高い領域で駆動されるデバイスに好ましく用いられる。 <Use of the organic electroluminescent device of the present invention>
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication. In particular, it is preferably used for a device that is driven in a region where light emission luminance is high, such as a light emitting device, a lighting device, and a display device.
本発明の発光装置は、本発明の有機電界発光素子を含むことを特徴とする。
次に、図2を参照して本発明の発光装置について説明する。
本発明の発光装置は、前記有機電界発光素子を用いてなる。
図2は、本発明の発光装置の一例を概略的に示した断面図である。図2の発光装置20は、透明基板(支持基板)2、有機電界発光素子10、封止容器16等により構成されている。 [Light emitting device]
The light emitting device of the present invention includes the organic electroluminescent element of the present invention.
Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The
ここで、接着層14としては、エポキシ樹脂等の光硬化型接着剤や熱硬化型接着剤を用いることができ、例えば熱硬化性の接着シートを用いることもできる。 The
Here, as the
本発明の照明装置は、本発明の有機電界発光素子を含むことを特徴とする。
次に、図3を参照して本発明の照明装置について説明する。
図3は、本発明の照明装置の一例を概略的に示した断面図である。本発明の照明装置40は、図3に示すように、前述した有機EL素子10と、光散乱部材30とを備えている。より具体的には、照明装置40は、有機EL素子10の基板2と光散乱部材30とが接触するように構成されている。
光散乱部材30は、光を散乱できるものであれば特に制限されないが、図3においては、透明基板31に微粒子32が分散した部材とされている。透明基板31としては、例えば、ガラス基板を好適に挙げることができる。微粒子32としては、透明樹脂微粒子を好適に挙げることができる。ガラス基板及び透明樹脂微粒子としては、いずれも、公知のものを使用できる。このような照明装置40は、有機電界発光素子10からの発光が散乱部材30の光入射面30Aに入射されると、入射光を光散乱部材30により散乱させ、散乱光を光出射面30Bから照明光として出射するものである。 [Lighting device]
The illuminating device of this invention is characterized by including the organic electroluminescent element of this invention.
Next, the illumination device of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention. As shown in FIG. 3, the
The
本発明の表示装置は、本発明の有機電界発光素子を含むことを特徴とする。
本発明の表示装置としては、例えば、テレビ、パーソナルコンピュータ、携帯電話、電子ペーパ等の表示装置とすることなどを挙げることができる。 [Display device]
The display device of the present invention includes the organic electroluminescent element of the present invention.
Examples of the display device of the present invention include a display device such as a television, a personal computer, a mobile phone, and electronic paper.
実施例および比較例で用いた化合物の構造式を以下にまとめて示す。 The features of the present invention will be described more specifically with reference to examples and comparative examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below.
The structural formulas of the compounds used in Examples and Comparative Examples are summarized below.
一般式(1)で表される化合物は、[0036]に記載の方法や、その他公知の反応を組み合わせて合成することができる。以下に一般式(1)で表される化合物の具体的合成手順の代表例を記載する。
合成中間体1を2.00g(4.01mmol)、ヨウ化メチルマグネシウム(3.0Mジエチルエーテル溶液)8.0mL(24.1mmol)、乾燥THF50mLを室温で混合した後、窒素雰囲気下、3時間加熱還流した。反応液を室温に戻した後、純水、酢酸エチルを加えて有機層を抽出した。有機層を濃縮した後、シリカゲルカラムクロマトグラフィー(展開溶媒:ヘキサン/酢酸エチル(4:1))により精製し、合成中間体2を0.80g得た(42%)。
合成中間体2を0.80g(1.70mmol)、メタンスルホン酸33mg(0.34mmol)、脱水塩化メチレン20mLを-78℃で混合し、窒素雰囲気下、室温まで自然に昇温しながら2時間攪拌した。反応後、析出した固形分を濾取し、この固体をトルエンで再結晶することにより化合物8を得た。
1H NMR(400MHz,in CDCl3);δ(ppm)=8.65(d,2H),8.29-8.21(m,6H),7.78-7.74(m,2H),7.43-7.39(m,4H),1.90(s,12H)ppm. 1. Synthesis Example The compound represented by the general formula (1) can be synthesized by combining the method described in [0036] and other known reactions. Below, the typical example of the specific synthetic | combination procedure of the compound represented by General formula (1) is described.
2.00 g (4.01 mmol) of synthetic intermediate 1, 8.0 mL (24.1 mmol) of methylmagnesium iodide (3.0 M diethyl ether solution), and 50 mL of dry THF were mixed at room temperature, and then under nitrogen atmosphere for 3 hours. Heated to reflux. After returning the reaction solution to room temperature, pure water and ethyl acetate were added to extract the organic layer. The organic layer was concentrated and purified by silica gel column chromatography (developing solvent: hexane / ethyl acetate (4: 1)) to obtain 0.80 g of synthetic intermediate 2 (42%).
Synthetic intermediate 2 0.80 g (1.70 mmol), methanesulfonic acid 33 mg (0.34 mmol) and
1 H NMR (400 MHz, in CDCl 3 ); δ (ppm) = 8.65 (d, 2H), 8.29-8.21 (m, 6H), 7.78-7.74 (m, 2H) , 7.43-7.39 (m, 4H), 1.90 (s, 12H) ppm.
(化合物6)
1H NMR(400MHz,in CDCl3);δ(ppm)=9.25(s,1H),8.41(d,2H),8.20(s,2H),8.15(s,2H),7.78(d,2H),7.48-7.41(m,4H),1.89(s,12H),1.60(s,9H)ppm.
(化合物12)
1H NMR(400MHz,in CDCl3);δ(ppm)=8.93(d,1H),8.48(d,1H),8.20-8.15(m,3H),8.07(s,1H),7.97(dd,1H),7.75(dd,1H),7.58(d,1H),7.50-7.33(m,4H),1.92(s,6H),1.74(s,6H),1.59(s,9H)ppm.
(化合物19)
1H NMR(400MHz,in CDCl3);δ(ppm)=8.30(s,1H),8.18(s,2H),8.10-8.05(m,2H),7.85(d,1H),7.52(d,1H),7.47(d,1H),7.30-7.25(m,4H),7.19(d,4H),7.09-7.02(m,5H),2.48(s,3H),1.93(s,6H),1.80(s,6H),1.59(s,9H)ppm.
(化合物20)
1H NMR(400MHz,in DMSO-d6);δ(ppm)=8.59(d,1H),8.33(s,1H),8.30-8.20(m,4H),8.08(s,2H),7.35(d,2H),7.27-7.17(m,4H),7.03(d,2H),6.86(d,1H),6.59(dd,1H),2.07(s,6H),1.62(s,6H),1.54(s,9H)ppm. The compounds 1 to 7 and 9 to 24 used in the examples were also synthesized by a method similar to that for compound 1. Below, the identification data of the
(Compound 6)
1 H NMR (400 MHz, in CDCl 3 ); δ (ppm) = 9.25 (s, 1H), 8.41 (d, 2H), 8.20 (s, 2H), 8.15 (s, 2H) ), 7.78 (d, 2H), 7.48-7.41 (m, 4H), 1.89 (s, 12H), 1.60 (s, 9H) ppm.
(Compound 12)
1 H NMR (400 MHz, in CDCl 3 ); δ (ppm) = 8.93 (d, 1H), 8.48 (d, 1H), 8.20-8.15 (m, 3H), 8.07 (S, 1H), 7.97 (dd, 1H), 7.75 (dd, 1H), 7.58 (d, 1H), 7.50-7.33 (m, 4H), 1.92 ( s, 6H), 1.74 (s, 6H), 1.59 (s, 9H) ppm.
(Compound 19)
1 H NMR (400 MHz, in CDCl 3 ); δ (ppm) = 8.30 (s, 1H), 8.18 (s, 2H), 8.10-8.05 (m, 2H), 7.85 (D, 1H), 7.52 (d, 1H), 7.47 (d, 1H), 7.30-7.25 (m, 4H), 7.19 (d, 4H), 7.09- 7.02 (m, 5H), 2.48 (s, 3H), 1.93 (s, 6H), 1.80 (s, 6H), 1.59 (s, 9H) ppm.
(Compound 20)
1 H NMR (400 MHz, in DMSO-d 6 ); δ (ppm) = 8.59 (d, 1H), 8.33 (s, 1H), 8.30-8.20 (m, 4H), 8 .08 (s, 2H), 7.35 (d, 2H), 7.27-7.17 (m, 4H), 7.03 (d, 2H), 6.86 (d, 1H), 6. 59 (dd, 1H), 2.07 (s, 6H), 1.62 (s, 6H), 1.54 (s, 9H) ppm.
(試験例1)分子間相互作用の評価
化合物1~24及び比較化合物1~6の各化合物について、真空TG-DTAにて重量が10%減少する温度を測定し、この温度を昇華温度とした。比較化合物1の昇華温度(単位:℃)/分子量を1.0としたときの相対値を表1にまとめた。この値が小さいほど分子間相互作用が低く、昇華性が高いことを示す。 2. Evaluation of physical properties of materials (Test Example 1) Evaluation of intermolecular interaction For each of compounds 1 to 24 and comparative compounds 1 to 6, the temperature at which the weight was reduced by 10% was measured with vacuum TG-DTA, and this temperature was sublimated. It was temperature. The relative values when the sublimation temperature (unit: ° C.) / Molecular weight of Comparative Compound 1 is 1.0 are shown in Table 1. Smaller values indicate lower intermolecular interactions and higher sublimation properties.
化合物1~24及び比較化合物1~6の各化合物1mgを電子工業用キシレン10mlに溶解させ、蛍光分光光度計(FP-6300、日本分光(株)製)にて発光スペクトルを測定した。このときの発光スペクトル半値幅β(発光極大値を1としたとき、0.5となる短波長と長波長のエネルギー差)に基づいて、色純度を以下の3段階で評価した。
○ β<0.25eV
△ 0.25≦β<0.30eV
× 0.30eV≦β (Test Example 2) Evaluation of color purity 1 mg of each of the compounds 1 to 24 and the comparative compounds 1 to 6 was dissolved in 10 ml of xylene for electronics industry, and was measured with a fluorescence spectrophotometer (FP-6300, manufactured by JASCO Corporation). The emission spectrum was measured. Based on the emission spectrum half width β at this time (when the emission maximum value is 1, the energy difference between the short wavelength and the long wavelength becomes 0.5), the color purity was evaluated in the following three stages.
○ β <0.25eV
Δ0.25 ≦ β <0.30eV
× 0.30eV ≦ β
厚み0.7mm、2.5cm角の石英ガラス基板上に、真空蒸着法にて、mCBPと各発光材料を質量比(95:5)となるように蒸着して膜厚50nmの薄膜を形成した。得られた膜に350nmのUV光を照射し、発光させたときの発光スペクトルを蛍光分光光度計(FP-6300、日本分光(株)製)を用いて測定し、色度(x、y)を求めた(CIE1931表色系)。このときのy値に基づいて、色度を以下の4段階で評価した。
◎ 0.05≦y≦0.10
○ 0.10<y≦0.15
△ 0.03≦y<0.05、0.15<y≦0.20
× y<0.03、0.20<y (Test Example 3) Evaluation of chromaticity mCBP and each light-emitting material were deposited on a quartz glass substrate having a thickness of 0.7 mm and a 2.5 cm square by a vacuum deposition method so as to have a mass ratio (95: 5). Thus, a thin film having a thickness of 50 nm was formed. The obtained film was irradiated with 350 nm UV light and emitted, and the emission spectrum was measured using a fluorescence spectrophotometer (FP-6300, manufactured by JASCO Corporation), and the chromaticity (x, y) (CIE 1931 color system). Based on the y value at this time, the chromaticity was evaluated in the following four stages.
◎ 0.05 ≦ y ≦ 0.10
○ 0.10 <y ≦ 0.15
Δ 0.03 ≦ y <0.05, 0.15 <y ≦ 0.20
X y <0.03, 0.20 <y
また、膜スペクトルおよび溶液スペクトルにおける発光スペクトル半値幅を算出し、溶液に対する膜の相対比(膜スペクトル半値幅/溶液スペクトル半値幅)を算出した。この値が1.0に近いほど、会合影響が小さくて、会合形成性が低くて好ましいと考えられる。 (Test Example 4) Evaluation of association formation property Further, the half-value width of the emission spectrum in the film spectrum and the solution spectrum was calculated, and the relative ratio of the film to the solution (the half-value width of the film spectrum / the half-value width of the solution spectrum) was calculated. It is considered that the closer this value is to 1.0, the smaller the influence of association and the better the formation of association.
有機電界発光素子の作製に用いた材料は全て昇華精製を行い、高速液体クロマトグラフィー(東ソーTSKgel ODS-100Z)により純度(254nmの吸収強度面積比)が99.9%以上であることを確認した。 3. Production and Evaluation of Organic Electroluminescent Device All materials used for producing the organic electroluminescent device were purified by sublimation, and the purity (absorption intensity area ratio at 254 nm) was 99.9 by high performance liquid chromatography (Tosoh TSKgel ODS-100Z). % Was confirmed.
厚み0.5mm、2.5cm角のITO膜を有するガラス基板(ジオマテック社製、表面抵抗10Ω/□)を洗浄容器に入れ、2-プロパノール中で超音波洗浄した後、30分間UV-オゾン処理を行った。この透明陽極(ITO膜)上に真空蒸着法にて以下の有機化合物層を順次蒸着した。
第1層:HAT-CN:膜厚10nm
第2層:NPD:膜厚30nm
第3層:H-1および表2中に記載の発光材料(質量比96:4):膜厚30nm
第4層:ET-1:膜厚30nm
この上に、フッ化リチウム1nm及び金属アルミニウム100nmをこの順に蒸着し陰極とした。
得られた積層体を、大気に触れさせることなく、窒素ガスで置換したグローブボックス内に入れ、ガラス製の封止缶及び紫外線硬化型の接着剤(XNR5516HV、長瀬チバ(株)製)を用いて封止し、発光部分が2mm×2mmの正方形である有機電界発光素子1-1~1-12、および比較用の有機電界発光素子1-1~1-4を得た。得られた各有機電界発光素子について、以下の試験を行った。 Example 1
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd.,
First layer: HAT-CN:
Second layer: NPD:
Third layer: H-1 and the light emitting materials described in Table 2 (mass ratio 96: 4):
Fourth layer: ET-1:
On this, 1 nm of lithium fluoride and 100 nm of metal aluminum were vapor-deposited in this order, and it was set as the cathode.
The obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. Thus, organic electroluminescent devices 1-1 to 1-12 having a light emitting portion of 2 mm × 2 mm square and comparative organic electroluminescent devices 1-1 to 1-4 were obtained. The following tests were performed on each organic electroluminescent element obtained.
東陽テクニカ製ソースメジャーユニット2400を用いて、直流電圧を各素子に印加して発光させ、その輝度を輝度計(BM-8、(株)トプコン社製)を用いて測定した。発光スペクトルと発光波長はスペクトルアナライザー(PMA-11、浜松ホトニクス(株)製)を用いて測定した。これらを元に輝度が1000cd/m2付近の外部量子効率(η)を輝度換算法により算出した。表2では比較素子1-1の値を1.0とした相対値で表示した。数字が大きいほど効率が良いことを示しているため、好ましい。 (A) Luminous efficiency Using a source measure unit 2400 manufactured by Toyo Technica, a DC voltage was applied to each element to emit light, and the luminance was measured using a luminance meter (BM-8, manufactured by Topcon Corporation). . The emission spectrum and emission wavelength were measured using a spectrum analyzer (PMA-11, manufactured by Hamamatsu Photonics). Based on these, the external quantum efficiency (η) with a luminance of around 1000 cd / m 2 was calculated by the luminance conversion method. In Table 2, the value of the comparative element 1-1 is displayed as a relative value with 1.0. A larger number indicates that the efficiency is better.
各有機電界発光素子を輝度が1000cd/m2となるように直流電圧を印加して発光させたときの発光スペクトルから色度(x、y)を求めた(CIE1931表色系)。このときのy値から以下の4段階で色度を評価した。
◎ 0.05≦y≦0.10
○ 0.10<y≦0.15
△ 0.04≦y<0.05、0.15<y≦0.20
× y<0.04、0.20<y (B) Chromaticity Chromaticity (x, y) was determined from the emission spectrum when each organic electroluminescent element was made to emit light by applying a DC voltage so that the luminance was 1000 cd / m 2 (CIE 1931 color system) ). The chromaticity was evaluated in the following four steps from the y value at this time.
◎ 0.05 ≦ y ≦ 0.10
○ 0.10 <y ≦ 0.15
Δ 0.04 ≦ y <0.05, 0.15 <y ≦ 0.20
X y <0.04, 0.20 <y
各有機電界発光素子を輝度が1000cd/m2になるように直流電圧を印加して発光させ続け、輝度が500cd/m2に低下したときの色度(x’、y’)を発光スペクトルから求めた。駆動劣化前後のy値の変化Δy(=|y’-Δy|)から、以下の3段階で駆動劣化後の色度変化を評価した。
○ Δy≦0.01
△ 0.01<Δy≦0.02、
× 0.02<Δy (C) Change in chromaticity after drive deterioration Chromaticity when each organic electroluminescent element is continuously caused to emit light by applying a DC voltage so that the luminance becomes 1000 cd / m 2 (the luminance decreases to 500 cd / m 2 ) x ′, y ′) were determined from the emission spectrum. From the change Δy (= | y′−Δy |) of the y value before and after driving deterioration, the chromaticity change after driving deterioration was evaluated in the following three stages.
○ Δy ≦ 0.01
Δ0.01 <Δy ≦ 0.02,
× 0.02 <Δy
層構成を以下に示すものに変えた以外は実施例1と同様にして有機電界発光素子を作製し、実施例1と同様の評価を行った。結果を表3に示す。なお、表3の発光効率は、比較素子2-1の外部量子効率を1.0としたときの相対値で表示している。
第1層:HI-2:膜厚10nm
第2層:HT-2:膜厚30nm
第3層:H-2及び表3中に記載の発光材料(質量比95:5):膜厚30nm
第4層:ET-2:膜厚10nm
第5層:ET-3:膜厚20nm (Example 2)
An organic electroluminescent element was produced in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 1 was performed. The results are shown in Table 3. The luminous efficiency in Table 3 is expressed as a relative value when the external quantum efficiency of the comparative element 2-1 is 1.0.
First layer: HI-2:
Second layer: HT-2:
Third layer: H-2 and light-emitting materials described in Table 3 (mass ratio 95: 5):
Fourth layer: ET-2:
5th layer: ET-3:
層構成を以下に示すものに変えた以外は実施例1と同様にして有機電界発光素子を作製し、実施例1と同様の評価を行った。結果を表4に示す。なお、表4の発光効率は、比較用の有機電界発光素子3-1の外部量子効率を1.0としたときの相対値で表示している。
第1層:HAT-CN:膜厚10nm
第2層:NPD:膜厚30nm
第3層:表4中に記載のホスト材料および発光材料(95:5):膜厚30nm
第4層:表4中に記載の電子輸送材料:膜厚30nm (Example 3)
An organic electroluminescent element was produced in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and the same evaluation as in Example 1 was performed. The results are shown in Table 4. The luminous efficiency in Table 4 is expressed as a relative value when the external quantum efficiency of the comparative organic electroluminescent device 3-1 is 1.0.
First layer: HAT-CN:
Second layer: NPD:
Third layer: Host material and light emitting material described in Table 4 (95: 5):
Fourth layer: Electron transport material described in Table 4:
-発光層形成用塗布液の調製-
発光材料2(0.1質量%)、ホスト材料H-4(0.9質量%)に、メチルエチルケトン(98.99質量%)を混合し、発光層形成用塗布液1を得た。
発光層形成用塗布液1において発光材料2を表5中に記載の発光材料に変更した以外は発光層形成用塗布液1と同様にして、表5に記載の発光材料を含む各発光層形成用塗布液を調製した。 Example 4
-Preparation of coating solution for light emitting layer formation-
Methyl ethyl ketone (99.99% by mass) was mixed with the light-emitting material 2 (0.1% by mass) and the host material H-4 (0.9% by mass) to obtain a coating solution 1 for forming a light-emitting layer.
Each light emitting layer formation containing the light emitting material described in Table 5 was performed in the same manner as the light emitting layer forming coating liquid 1 except that the
25mm×25mm×0.7mmのガラス基板上にITOを150nmの厚みで蒸着し製膜したものを透明支持基板とした。この透明支持基板をエッチング、洗浄した。
このITOガラス基板上に、下記構造式で表されるPTPDES-2(ケミプロ化成製、Tg=205℃)2質量部を電子工業用シクロヘキサノン(関東化学製)98質量部に溶解し、厚みが約40nmとなるようにスピンコート(2,000rpm、20秒間、)した後、120℃で30分間乾燥と160℃で10分間アニール処理することで、正孔注入層を成膜した。 -Fabrication of organic electroluminescent elements-
A transparent support substrate was formed by depositing ITO to a thickness of 150 nm on a 25 mm × 25 mm × 0.7 mm glass substrate. This transparent support substrate was etched and washed.
On this ITO glass substrate, 2 parts by mass of PTPDES-2 (Kemipro Kasei, Tg = 205 ° C.) represented by the following structural formula was dissolved in 98 parts by mass of cyclohexanone for electronics industry (manufactured by Kanto Chemical), and the thickness was about After spin coating (2,000 rpm, 20 seconds) to 40 nm, a hole injection layer was formed by drying at 120 ° C. for 30 minutes and annealing at 160 ° C. for 10 minutes.
次いで、発光層上に、電子輸送層として、下記構造式で表されるBAlq(ビス-(2-メチル-8-キノリノラト)-4-(フェニル-フェノラト)-アルミニウム(III))を、厚みが40nmとなるように真空蒸着法にて形成した。
以上により作製した積層体を、アルゴンガスで置換したグロ-ブボックス内に入れ、ステンレス製の封止缶及び紫外線硬化型の接着剤(XNR5516HV、長瀬チバ(株)製)を用いて封止することで、有機電界発光素子4-1を作製した。
また、発光材料を表5に示すように変更した発光層形成用塗布液を用いた以外は、有機電界発光素子4-1と同様にして有機電界発光素子4-2~4-5、比較素子4-1~4-2を作製し、実施例1と同様の評価を行った。結果を表5に示す。なお、表5の発光効率は、比較用の有機電界発光素子4-1の外部量子効率を1.0としたときの相対値で表示している。 On the hole injection layer, the light emitting layer forming coating solution 1 was spin-coated (1,300 rpm, 30 seconds) so as to have a thickness of about 40 nm to obtain a light emitting layer.
Next, BAlq (bis- (2-methyl-8-quinolinolato) -4- (phenyl-phenolato) -aluminum (III)) represented by the following structural formula is formed on the light emitting layer as an electron transport layer with a thickness of It formed by the vacuum evaporation method so that it might become 40 nm.
The laminate produced as described above is placed in a glove box substituted with argon gas, and sealed with a stainless steel sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.). Thus, an organic electroluminescent element 4-1 was produced.
Further, the organic electroluminescent elements 4-2 to 4-5 and the comparative element were the same as the organic electroluminescent element 4-1, except that the light emitting material was changed to the coating solution for forming the light emitting layer as shown in Table 5. 4-1 to 4-2 were prepared and evaluated in the same manner as in Example 1. The results are shown in Table 5. The luminous efficiency in Table 5 is expressed as a relative value when the external quantum efficiency of the comparative organic electroluminescent element 4-1 is 1.0.
3・・・陽極
4・・・正孔注入層
5・・・正孔輸送層
6・・・発光層
7・・・正孔ブロック層
8・・・電子輸送層
9・・・陰極
10・・・有機電界発光素子
11・・・有機層
12・・・保護層
14・・・接着層
16・・・封止容器
20・・・発光装置
30・・・光散乱部材
31・・・透明基板
30A・・光入射面
30B・・光出射面
32・・・微粒子
40・・・照明装置 DESCRIPTION OF
Claims (25)
- 基板と、
該基板上に配置され、陽極及び陰極を含む一対の電極と、
該電極間に配置された有機層とを有し、
前記有機層が、下記一般式(1)で表される化合物を含有することを特徴とする有機電界発光素子。
A pair of electrodes disposed on the substrate, including an anode and a cathode;
An organic layer disposed between the electrodes,
The said organic layer contains the compound represented by following General formula (1), The organic electroluminescent element characterized by the above-mentioned.
- 前記一般式(1)において、XはCRaRb(Ra、Rbはそれぞれ独立に水素原子または置換基を表し、RaとRbは共同して5または6員環を形成していてもよい。)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。 In the general formula (1), X represents CR a R b (R a and R b each independently represents a hydrogen atom or a substituent, and R a and R b jointly form a 5- or 6-membered ring. The organic electroluminescent element according to claim 1, wherein
- 前記一般式(1)において、R1~R8の少なくとも一つがフッ素原子、アルキル基、シリル基のいずれかを有する置換基であることを特徴とする請求項1または2に記載の有機電界発光素子。 3. The organic electroluminescence according to claim 1, wherein at least one of R 1 to R 8 in the general formula (1) is a substituent having any one of a fluorine atom, an alkyl group, and a silyl group. element.
- 前記一般式(1)において、A1~A4が全てCRf(Rfは水素原子または置換基を表し、隣り合う2つのCRfは共同して5または6員環を形成していてもよい。)であることを特徴とする請求項1~3のいずれか一項に記載の有機電界発光素子。 In the general formula (1), A 1 to A 4 are all CR f (R f represents a hydrogen atom or a substituent, and two adjacent CR f may jointly form a 5- or 6-membered ring. The organic electroluminescent device according to any one of claims 1 to 3, wherein the organic electroluminescent device is good.
- 前記一般式(1)で表される化合物が下記一般式(2)で表され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。
- 前記一般式(2)において、R10が-NRc'Rd'基(Rc'、Rd'はそれぞれ独立に置換基)であることを特徴とする請求項5に記載の有機電界発光素子。 6. The organic electroluminescence according to claim 5, wherein in the general formula (2), R 10 is a —NR c ′ R d ′ group (R c ′ and R d ′ are each independently a substituent). element.
- 前記一般式(1)で表される化合物が下記一般式(3)で表され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。
- 前記一般式(1)で表される化合物が下記一般式(4)で表され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。
- 前記一般式(1)で表される化合物が下記一般式(5)で表され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。
- 前記一般式(1)で表される化合物の分子量が800以下であることを特徴とする請求項1~9のいずれか一項に記載の有機電界発光素子。 The organic electroluminescent element according to any one of claims 1 to 9, wherein the compound represented by the general formula (1) has a molecular weight of 800 or less.
- 前記一般式(1)で表される化合物を含む有機層が発光層であることを特徴とする請求項1~10のいずれか一項に記載の有機電界発光素子。 11. The organic electroluminescent device according to claim 1, wherein the organic layer containing the compound represented by the general formula (1) is a light emitting layer.
- 前記一般式(1)で表される化合物が発光材料であることを特徴とする請求項1~11のいずれか一項に記載の有機電界発光素子。 The organic electroluminescent device according to any one of claims 1 to 11, wherein the compound represented by the general formula (1) is a luminescent material.
- 前記有機層の少なくとも一層に下記一般式(An-1)で表される化合物を含むことを特徴とする請求項1~12のいずれかに記載の有機電界発光素子。
- 前記一般式(An-1)で表される化合物が、下記(An-2)で表される化合物であることを特徴とする請求項13に記載の有機電界発光素子。
- 前記一般式(An-1)で表される化合物を含む少なくとも一層の有機層が前記発光層であることを特徴とする請求項13または14に記載の有機電界発光素子。 15. The organic electroluminescent element according to claim 13, wherein at least one organic layer containing the compound represented by the general formula (An-1) is the light emitting layer.
- 前記有機層の少なくとも一層に下記一般式(P)で表される化合物を含むことを特徴とする請求項1~15のいずれか一項に記載の有機電界発光素子。
- 前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-1)で表される置換基を有する化合物であることを特徴とする請求項16に記載の有機電界発光素子。 The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-1) as at least one of R P. Organic electroluminescent element.
- 前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-2)で表される置換基を有する化合物であることを特徴とする請求項16に記載の有機電界発光素子。 The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-2) as at least one of R P. Organic electroluminescent element.
- 前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-3)で表される置換基を有する化合物であることを特徴とする請求項16に記載の有機電界発光素子。 The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-3) as at least one of R P. Organic electroluminescent element.
- 前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-4)で表される置換基を有する化合物であることを特徴とする請求項16に記載の有機電界発光素子。 The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-4) as at least one of R P. Organic electroluminescent element.
- 前記一般式(P)で表される化合物が、RPのうち少なくとも一つとして前記一般式(P-5)で表される置換基を有する化合物であることを特徴とする請求項16に記載の有機電界発光素子。 The compound represented by the general formula (P) is a compound having a substituent represented by the general formula (P-5) as at least one of R P. Organic electroluminescent element.
- 前記一般式(1)で表される化合物を含む有機層が真空蒸着プロセスにて形成されてなることを特徴とする請求項1~21のいずれか一項に記載の有機電界発光素子。 The organic electroluminescent element according to any one of claims 1 to 21, wherein an organic layer containing the compound represented by the general formula (1) is formed by a vacuum deposition process.
- 前記一般式(1)で表される化合物を含む有機層が湿式プロセスにて形成されてなることを特徴とする請求項1~21のいずれか一項に記載の有機電界発光素子。 The organic electroluminescent element according to any one of claims 1 to 21, wherein an organic layer containing the compound represented by the general formula (1) is formed by a wet process.
- 請求項1~23のいずれか一項に記載の有機電界発光素子を用いたことを特徴とする発光装置、表示装置または照明装置。 A light emitting device, a display device, or an illumination device using the organic electroluminescent element according to any one of claims 1 to 23.
- 下記一般式(1)で表される化合物。
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- 2012-04-12 WO PCT/JP2012/060027 patent/WO2012141249A1/en active Application Filing
- 2012-04-12 KR KR1020137026607A patent/KR102034905B1/en active IP Right Grant
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WO2018099433A1 (en) * | 2016-11-30 | 2018-06-07 | 广州华睿光电材料有限公司 | Fused ring compound and use thereof, mixture and organic electronic device |
CN109790456A (en) * | 2016-11-30 | 2019-05-21 | 广州华睿光电材料有限公司 | Fused ring compound and its application, mixture, organic electronic device |
Also Published As
Publication number | Publication date |
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KR102034905B1 (en) | 2019-10-21 |
KR20140027948A (en) | 2014-03-07 |
JP5979947B2 (en) | 2016-08-31 |
JP2012231136A (en) | 2012-11-22 |
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