JP6750783B2 - Compound and organic light emitting device using the same - Google Patents
Compound and organic light emitting device using the same Download PDFInfo
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- JP6750783B2 JP6750783B2 JP2018548405A JP2018548405A JP6750783B2 JP 6750783 B2 JP6750783 B2 JP 6750783B2 JP 2018548405 A JP2018548405 A JP 2018548405A JP 2018548405 A JP2018548405 A JP 2018548405A JP 6750783 B2 JP6750783 B2 JP 6750783B2
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- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
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- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical group 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
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Description
本明細書は、有機化合物およびこれを用いる有機発光素子に関する。本明細書は、２０１６年３月３０日付で韓国特許庁に出願された韓国特許出願第１０−２０１６−００３８４６４号の出願日の利益を主張し、その内容はすべて本明細書に組み込まれる。 The present specification relates to an organic compound and an organic light emitting device using the same. This specification claims the benefit of the filing date of Korean Patent Application No. 10-2016-0038464 filed with the Korean Patent Office on March 30, 2016, the entire contents of which are incorporated herein.
一般的に、有機発光現象とは、有機物質を用いて電気エネルギーを光エネルギーに変換させる現象をいう。有機発光現象を利用する有機発光素子は、通常、陽極および陰極と、それらの間に有機物層とを含む構造を有する。ここで、有機物層は、有機発光素子の効率と安定性を高めるためにそれぞれ異なる物質で構成された多層の構造からなる場合が多く、例えば、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層などからなる。このような有機発光素子の構造において、２つの電極の間に電圧をかけると、陽極からは正孔が、陰極からは電子が有機物層に注入され、注入された正孔と電子が接した時、エキシトン（ｅｘｃｉｔｏｎ）が形成され、このエキシトンが再び基底状態に落ちる時に光を発する。 Generally, the organic light emitting phenomenon is a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting device that utilizes the organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer between them. Here, the organic material layer is often composed of a multi-layered structure composed of different materials in order to enhance the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, It is composed of an electron transport layer, an electron injection layer and the like. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode, and the injected holes come into contact with the electrons. , Excitons are formed and emit light when the excitons fall back to the ground state.
前記のような有機発光素子のための新たな材料の開発が求められ続けている。 The development of new materials for the above organic light emitting devices continues to be required.
本明細書には、化合物およびこれを含む有機発光素子が記載される。 Described herein are compounds and organic light emitting devices that include the same.
本明細書の一実施態様は、下記化学式１で表される化合物を提供する。
［化学式１］
Ｒは、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；シアノ基；置換もしくは非置換の炭素数１〜２０のアルキル基；置換もしくは非置換の炭素数３〜２０のシクロアルキル基；置換もしくは非置換の炭素数６〜２０の単環もしくは多環のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環のヘテロ環基であり、
Ａｒ１、Ａｒ２および−Ｌ−（Ｙ）ｎは、互いに異なり、
Ａｒ１およびＡｒ２は、互いに異なり、それぞれ独立に、水素；重水素；置換もしくは非置換の炭素数１〜２０のアルキル基；置換もしくは非置換の炭素数６〜２０の単環もしくは多環のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環のヘテロ環基であり、
Ｌは、直接結合；置換もしくは非置換の炭素数６〜２０の単環もしくは多環の２価〜６価のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環の２価〜６価のヘテロアリール基であり、
Ｙは、ナフチル基；フェナントレン基；ジメチルフルオレン基；アントラセン基；トリフェニレン基；ピレン基；テトラセン基；クリセン基；ペリレン基；またはフルオランテン基であり、
ｎは、２〜５の整数であり、複数のＹは、同一または異なる。
One embodiment of the present specification provides a compound represented by Chemical Formula 1 below.
[Chemical formula 1]
R's are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms. A group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,
Ar1, Ar2 and -L-(Y)n are different from each other,
Ar1 and Ar2 are different from each other, and each independently, hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms. Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,
L is a direct bond; a substituted or unsubstituted monocyclic or polycyclic divalent to hexavalent aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic group having 3 to 20 carbon atoms. A divalent to hexavalent heteroaryl group,
Y is a naphthyl group; a phenanthrene group; a dimethylfluorene group; an anthracene group; a triphenylene group; a pyrene group; a tetracene group; a chrysene group; a perylene group; or a fluoranthene group,
n is an integer of 2 to 5, and a plurality of Ys are the same or different.
また、本明細書の一実施態様は、第１電極と、前記第１電極に対向して備えられた第２電極と、前記第１電極と前記第２電極との間に備えられた１層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの１層以上は、前記化学式１の化合物を含むものである有機発光素子を提供する。 Further, one embodiment of the present specification is directed to a first electrode, a second electrode provided so as to face the first electrode, and a single layer provided between the first electrode and the second electrode. An organic light emitting device including the above organic material layer, wherein at least one layer of the organic material layers includes the compound of Chemical Formula 1.
本明細書に記載の化合物は、有機発光素子の有機物層の材料として使用できる。少なくとも一つの実施態様に係る化合物は、有機発光素子において効率の向上、低い駆動電圧および／または寿命特性を向上させることができる。特に、本明細書に記載の化合物は、正孔注入、正孔輸送、正孔注入および輸送、発光、電子輸送、または電子注入材料として使用可能であり、好ましくは、発光層、電子輸送層、または電子注入層の材料として使用可能である。 The compounds described in the present specification can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one embodiment may improve efficiency, low driving voltage, and/or life characteristics of an organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting or electron injecting materials, preferably light emitting layers, electron transporting layers, Alternatively, it can be used as a material for the electron injection layer.
以下、本明細書についてより詳細に説明する。 Hereinafter, the present specification will be described in more detail.
本明細書の一実施態様は、前記化学式１で表される化合物を提供する。 One embodiment of the present specification provides a compound represented by Formula 1 above.
前記置換基の例示は以下に説明するが、これに限定されるものではない。 Examples of the substituent are described below, but the substituent is not limited thereto.
本明細書において、「置換もしくは非置換の」という用語は、重水素；ハロゲン基；ニトリル基；ニトロ基；アミノ基；アルキル基；シクロアルキル基；アルケニル基；アリール基；およびヘテロ環基からなる群より選択された１個以上の置換基で置換もしくは非置換であるか、前記例示された置換基のうち２以上の置換基が連結された置換もしくは非置換であることを意味する。例えば、２以上の置換基が連結された置換基は、ビフェニル基であってもよい。すなわち、ビフェニル基は、アリール基であってもよく、２個のフェニル基が連結された置換基と解釈される。 In the present specification, the term “substituted or unsubstituted” is composed of deuterium; a halogen group; a nitrile group; a nitro group; an amino group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; and a heterocyclic group. It means that it is substituted or unsubstituted by one or more substituents selected from the group, or is substituted or unsubstituted by connecting two or more substituents among the exemplified substituents. For example, the substituent in which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group, and is interpreted as a substituent in which two phenyl groups are linked.
本明細書において、前記アルキル基は、直鎖もしくは分枝鎖であってもよく、炭素数は特に限定されないが、１〜４０のものが好ましい。一実施態様によれば、前記アルキル基の炭素数は１〜２０である。もう一つの実施態様によれば、前記アルキル基の炭素数は１〜１０である。もう一つの実施態様によれば、前記アルキル基の炭素数は１〜６である。アルキル基の具体例としては、メチル、エチル、プロピル、ｎ−プロピル、イソプロピル、ブチル、ｎ−ブチル、イソブチル、ｔｅｒｔ−ブチル、ｓｅｃ−ブチル、１−メチル−ブチル、１−エチル−ブチル、ペンチル、ｎ−ペンチル、イソペンチル、ネオペンチル、ｔｅｒｔ−ペンチル、ヘキシル、ｎ−ヘキシル、１−メチルペンチル、２−メチルペンチル、４−メチル−２−ペンチル、３，３−ジメチルブチル、２−エチルブチル、ヘプチル、ｎ−ヘプチル、１−メチルヘキシル、シクロペンチルメチル、シクロヘキシルメチル、オクチル、ｎ−オクチル、ｔｅｒｔ−オクチル、１−メチルヘプチル、２−エチルヘキシル、２−プロピルペンチル、ｎ−ノニル、２，２−ジメチルヘプチル、１−エチル−プロピル、１，１−ジメチル−プロピル、イソヘキシル、４−メチルヘキシル、５−メチルヘキシルなどがあるが、これらに限定されない。 In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but one having 1 to 40 carbon atoms is preferable. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1 -Ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but not limited thereto.
本明細書において、前記アルケニル基は、直鎖もしくは分枝鎖であってもよく、炭素数は特に限定されないが、２〜４０のものが好ましい。一実施態様によれば、前記アルケニル基の炭素数は２〜２０である。もう一つの実施態様によれば、前記アルケニル基の炭素数は２〜１０である。もう一つの実施態様によれば、前記アルケニル基の炭素数は２〜６である。具体例としては、ビニル、１−プロペニル、イソプロペニル、１−ブテニル、２−ブテニル、３−ブテニル、１−ペンテニル、２−ペンテニル、３−ペンテニル、３−メチル−１−ブテニル、１，３−ブタジエニル、アリル、１−フェニルビニル−１−イル、２−フェニルビニル−１−イル、２，２−ジフェニルビニル−１−イル、２−フェニル−２−（ナフチル−１−イル）ビニル−１−イル、２，２−ビス（ジフェニル−１−イル）ビニル−１−イル、スチルベニル基、スチレニル基などがあるが、これらに限定されない。 In the present specification, the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-. Butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1- Examples include, but are not limited to, yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like.
本明細書において、シクロアルキル基は特に限定されないが、炭素数３〜６０のものが好ましく、一実施態様によれば、前記シクロアルキル基の炭素数は３〜３０である。もう一つの実施態様によれば、前記シクロアルキル基の炭素数は３〜２０である。もう一つの実施態様によれば、前記シクロアルキル基の炭素数は３〜６である。具体的には、シクロプロピル、シクロブチル、シクロペンチル、３−メチルシクロペンチル、２，３−ジメチルシクロペンチル、シクロヘキシル、３−メチルシクロヘキシル、４−メチルシクロヘキシル、２，３−ジメチルシクロヘキシル、３，４，５−トリメチルシクロヘキシル、４−ｔｅｒｔ−ブチルシクロヘキシル、シクロヘプチル、シクロオクチルなどがあるが、これらに限定されない。 In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethyl. Examples include, but are not limited to, cyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
本明細書において、アリール基は特に限定されないが、炭素数６〜６０のものが好ましく、単環式アリール基もしくは多環式アリール基であってもよい。一実施態様によれば、前記アリール基の炭素数は６〜３０である。一実施態様によれば、前記アリール基の炭素数は６〜２０である。前記アリール基が、単環式アリール基としては、フェニル基、ビフェニル基、ターフェニル基などになってもよいが、これらに限定されるものではない。前記多環式アリール基としては、ナフチル基、アントラセニル基、フェナントリル基、ピレニル基、ペリレニル基、クリセニル基、フルオレニル基などになってもよいが、これらに限定されるものではない。 In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the aryl group has 6 to 30 carbon atoms. In one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, but is not limited thereto.
前記フルオレニル基が置換される場合、
本明細書において、ヘテロ環基は、異種元素としてＯ、Ｎ、Ｓ、Ｓｉ、およびＳｅのうちの１個以上を含むヘテロ環基であって、炭素数は特に限定されないが、炭素数２〜６０のものが好ましい。ヘテロ環基の例としては、チオフェン基、フラン基、ピロール基、イミダゾール基、チアゾール基、オキサゾール基、オキサジアゾール基、ピリジル基、ビピリジル基、ピリミジル基、トリアジン基、トリアゾール基、アクリジル基、ピリダジン基、ピラジニル基、キノリニル基、キナゾリン基、キノキサリニル基、フタラジニル基、ピリドピリミジニル基、ピリドピラジニル基、ピラジノピラジニル基、イソキノリン基、インドール基、カルバゾール基、ベンズオキサゾール基、ベンズイミダゾール基、ベンゾチアゾール基、ベンゾカルバゾール基、ベンゾチオフェン基、ジベンゾチオフェン基、ベンゾフラニル基、フェナントロリン基（ｐｈｅｎａｎｔｈｒｏｌｉｎｅ）、イソオキサゾリル基、チアジアゾリル基、フェノチアジニル基、およびジベンゾフラニル基などがあるが、これらにのみ限定されるものではない。 In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, S, Si, and Se as a different element, and the carbon number is not particularly limited, but it is 2 to 2 carbon atoms. 60 is preferable. Examples of the heterocyclic group are thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group. Group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzo Examples include, but are not limited to, thiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl. Not a thing.
本明細書において、ヘテロ環基は、単環もしくは多環であってもよいし、芳香族、脂肪族、または芳香族と脂肪族との縮合環であってもよいし、前記ヘテロアリール基の例示の中から選択されてもよい。 In the present specification, the heterocyclic group may be a monocyclic ring or a polycyclic ring, an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring. It may be selected from the examples.
本明細書において、前記縮合構造は、当該置換基に芳香族炭化水素環が縮合された構造であってもよい。例えば、ベンズイミダゾールの縮合環として、
本明細書において、アリーレンは、２価の基であることを除けば、前述したアリール基に関する説明が適用可能である。 In the present specification, the description regarding the aryl group described above is applicable, except that the arylene is a divalent group.
本明細書において、ヘテロアリーレンは、２価の基であることを除けば、前述したヘテロ環基に関する説明が適用可能である。 In the present specification, the description about the heterocyclic group described above is applicable, except that the heteroarylene is a divalent group.
本明細書の一実施態様において、前記Ｘ１は、Ｎであり、Ｘ２およびＸ３は、ＣＲである。 In one embodiment of the present specification, X1 is N and X2 and X3 are CR.
本明細書の一実施態様において、前記Ｘ２は、Ｎであり、Ｘ１およびＸ３は、ＣＲである。 In one embodiment of the present specification, X2 is N and X1 and X3 are CR.
本明細書の一実施態様において、前記Ｘ１およびＸ２は、Ｎであり、Ｘ３は、ＣＲである。 In one embodiment of the present specification, X1 and X2 are N and X3 is CR.
本明細書の一実施態様において、前記Ｘ２およびＸ３は、Ｎであり、Ｘ１は、ＣＲである。 In one embodiment of the present specification, X2 and X3 are N and X1 is CR.
本明細書の一実施態様において、前記Ｘ１〜Ｘ３は、Ｎである。 In one embodiment of the present specification, X1 to X3 are N.
本明細書の一実施態様において、前記Ｒは、水素または重水素である。 In one embodiment of the present specification, R is hydrogen or deuterium.
本明細書の一実施態様において、前記Ｒは、水素である。 In one embodiment of the present specification, R is hydrogen.
本明細書の一実施態様において、前記Ａｒ１およびＡｒ２は、互いに異なり、それぞれ独立に、置換もしくは非置換の炭素数６〜２０の単環もしくは多環のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環のヘテロ環基である。 In one embodiment of the present specification, Ar 1 and Ar 2 are different from each other, and each independently, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted carbon number 3 to 20 monocyclic or polycyclic heterocyclic groups.
本明細書の一実施態様において、前記Ａｒ１およびＡｒ２は、互いに異なり、それぞれ独立に、置換もしくは非置換の炭素数６〜２０の単環もしくは多環のアリール基である。 In one embodiment of the present specification, Ar 1 and Ar 2 are different from each other, and each independently represent a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
本明細書の一実施態様において、前記Ａｒ１およびＡｒ２は、互いに異なり、それぞれ独立に、置換もしくは非置換のフェニル基；置換もしくは非置換のビフェニル基；置換もしくは非置換のフェナントレン基；置換もしくは非置換のジメチルフルオレン基；置換もしくは非置換のジベンゾフラン基；置換もしくは非置換のジベンゾチオフェン基；置換もしくは非置換のナフチル基、または置換もしくは非置換のピレン基である。 In one embodiment of the present specification, Ar1 and Ar2 are different from each other, and each independently, a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted A dimethylfluorene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyrene group.
本明細書の一実施態様において、前記Ａｒ１およびＡｒ２は、互いに異なり、それぞれ独立に、フェニル基；ビフェニル基；フェナントレン基；ジメチルフルオレン基；ジベンゾフラン基；ジベンゾチオフェン基；ナフチル基またはピレン基である。 In one embodiment of the present specification, Ar1 and Ar2 are different from each other and independently represent a phenyl group; a biphenyl group; a phenanthrene group; a dimethylfluorene group; a dibenzofuran group; a dibenzothiophene group; a naphthyl group or a pyrene group.
本明細書の一実施態様において、前記Ａｒ１は、フェニル基であり、Ａｒ２は、ビフェニル基；フェナントレン基；ジメチルフルオレン基；ジベンゾフラン基；ジベンゾチオフェン基；ナフチル基またはピレン基である。 In one embodiment of the present specification, Ar1 is a phenyl group, and Ar2 is a biphenyl group; a phenanthrene group; a dimethylfluorene group; a dibenzofuran group; a dibenzothiophene group; a naphthyl group or a pyrene group.
本明細書の一実施態様において、前記Ｌは、置換もしくは非置換の炭素数６〜２０の単環もしくは多環の２価〜４価のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環の２価〜４価のヘテロアリール基である。 In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted C 3 to 20 carbon atom. Is a monocyclic or polycyclic divalent to tetravalent heteroaryl group.
本明細書の一実施態様において、前記Ｌは、置換もしくは非置換の炭素数６〜２０の単環もしくは多環の２価〜４価のアリール基である。 In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic divalent to tetravalent aryl group having 6 to 20 carbon atoms.
本明細書の一実施態様において、前記Ｌは、置換もしくは非置換の炭素数６〜２０の単環もしくは多環の３価のアリール基である。 In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic trivalent aryl group having 6 to 20 carbon atoms.
本明細書の一実施態様において、前記Ｌは、２価〜４価のフェニル基；２価〜４価のビフェニル基；２価〜４価のナフチル基；２価〜４価のフェナントレン基；２価〜４価のカルバゾール基；２価〜４価のピリジン基；２価〜４価のピリミジン基；２価〜４価のトリアジン基；２価〜４価のキノリン基；２価〜４価のジベンゾフラン基；または２価〜４価のジベンゾチオフェン基である。 In one embodiment of the present specification, L is a divalent to tetravalent phenyl group; a divalent to tetravalent biphenyl group; a divalent to tetravalent naphthyl group; a divalent to tetravalent phenanthrene group; 2 Divalent to tetravalent carbazole group; divalent to tetravalent pyridine group; divalent to tetravalent pyrimidine group; divalent to tetravalent triazine group; divalent to tetravalent quinoline group; divalent to tetravalent A dibenzofuran group; or a divalent to tetravalent dibenzothiophene group.
本明細書の一実施態様において、前記Ｌは、置換もしくは非置換の３価のフェニル基；置換もしくは非置換の３価のビフェニル基；置換もしくは非置換の３価のフェナントレン基；置換もしくは非置換の３価のジメチルフルオレン基；置換もしくは非置換の３価のジベンゾフラン基；置換もしくは非置換の３価のジベンゾチオフェン基；置換もしくは非置換の３価のナフチル基または置換もしくは非置換の３価のピレン基である。 In one embodiment of the present specification, L is a substituted or unsubstituted trivalent phenyl group; a substituted or unsubstituted trivalent biphenyl group; a substituted or unsubstituted trivalent phenanthrene group; a substituted or unsubstituted A trivalent dimethylfluorene group; a substituted or unsubstituted trivalent dibenzofuran group; a substituted or unsubstituted trivalent dibenzothiophene group; a substituted or unsubstituted trivalent naphthyl group or a substituted or unsubstituted trivalent group It is a pyrene group.
本明細書の一実施態様において、前記Ｌは、２価〜４価のフェニル基；２価〜４価のビフェニル基；２価〜４価のフェナントレン基；２価〜４価のジメチルフルオレン基；２価〜４価のジベンゾフラン基；２価〜４価のジベンゾチオフェン基；２価〜４価のナフチル基または２価〜４価のピレン基である。 In one embodiment of the present specification, L is a divalent to tetravalent phenyl group; a divalent to tetravalent biphenyl group; a divalent to tetravalent phenanthrene group; a divalent to tetravalent dimethylfluorene group; A divalent to tetravalent dibenzofuran group; a divalent to tetravalent dibenzothiophene group; a divalent to tetravalent naphthyl group or a divalent to tetravalent pyrene group.
本明細書の一実施態様において、前記Ｌは、３価のフェニレン基；３価のビフェニリレン基；３価のフェナントレン基；３価のジメチルフルオレン基；３価のジベンゾフラン基；３価のジベンゾチオフェン基；３価のナフチル基または３価のピレン基である。 In one embodiment of the present specification, L is a trivalent phenylene group; a trivalent biphenylylene group; a trivalent phenanthrene group; a trivalent dimethylfluorene group; a trivalent dibenzofuran group; a trivalent dibenzothiophene group A trivalent naphthyl group or a trivalent pyrene group.
本明細書の一実施態様において、前記Ｌは、２価〜４価のフェニル基または２価〜４価のビフェニル基である。 In one embodiment of the present specification, L is a divalent to tetravalent phenyl group or a divalent to tetravalent biphenyl group.
本明細書の一実施態様において、前記Ｌは、３価のフェニル基または３価のビフェニル基である。 In one embodiment of the present specification, L is a trivalent phenyl group or a trivalent biphenyl group.
本明細書の一実施態様において、前記Ｙは、下記構造式の中から選択される。
本明細書の一実施態様において、前記Ｙは、ナフチル基またはフェナントレン基である。 In one embodiment of the present specification, Y is a naphthyl group or a phenanthrene group.
本明細書の一実施態様において、前記複数のＹは、異なる。 In one embodiment of the present specification, the plurality of Ys are different.
本明細書の一実施態様において、前記複数のＹは、同一である。 In one embodiment of the present specification, the plurality of Ys are the same.
本明細書の一実施態様において、前記化学式１の化合物は、下記構造式の中から選択されたいずれか１つである。
本出願の一実施態様に係る化合物は、後述する製造方法で製造される。 The compound according to one embodiment of the present application is produced by the production method described below.
例えば、前記化学式１の化合物は、下記反応式１のようにコア構造が製造される。置換基は、当技術分野で知られている方法により結合することができ、置換基の種類、位置または個数は、当技術分野で知られている技術により変更可能である。
［反応式１］
[Reaction formula 1]
化学式Ａのような当量のビス（ピナコラト）ジボロン（Ｂｉｓ（ｐｉｎａｃｏｌａｔｏ）ｄｉｂｏｒｏｎ）をジオキサン溶液（ｄｉｏｘａｎｅ ｓｏｌｖｅｎｔ）に入れて、ＫＯＡｃおよびＰｄを触媒としてボリレーション（ｂｏｒｙｌａｔｉｏｎ）反応を進行させて化学式Ｂの化合物を得ることができる。 An equivalent amount of bis(pinacolato)diboron as represented by Chemical Formula A is added to a dioxane solution, and a boration reaction is promoted by using KOAc and Pd as a catalyst to advance the compound of Chemical Formula B. Can be obtained.
化学式Ｂの化合物と化合物Ｙとのカップリング反応により化学式１のコア構造を得ることができる。 The core structure of Chemical Formula 1 can be obtained by the coupling reaction of the compound of Chemical Formula B and the compound Y.
また、本明細書は、前述した化合物を含む有機発光素子を提供する。 The present specification also provides an organic light emitting device that includes the compound described above.
本出願の一実施態様において、第１電極と、前記第１電極に対向して備えられた第２電極と、前記第１電極と前記第２電極との間に備えられた１層以上の有機物層とを含む有機発光素子であって、前記有機物層のうちの１層以上は、前記化合物を含むものである有機発光素子を提供する。 In one embodiment of the present application, a first electrode, a second electrode provided to face the first electrode, and one or more layers of organic material provided between the first electrode and the second electrode. An organic light emitting device including a layer, wherein at least one layer of the organic material layers includes the compound.
本明細書において、ある部材が他の部材の「上に」位置しているとする時、これは、ある部材が他の部材に接している場合のみならず、２つの部材の間にさらに他の部材が存在する場合も含む。 As used herein, when a member is "above" another member, this means not only when one member is in contact with another member, but also between two members. Including the case where the member of
本明細書において、ある部分がある構成要素を「含む」とする時、これは、特に反対の記載がない限り、他の構成要素を除くのではなく、他の構成要素をさらに包含できることを意味する。 In this specification, when a part is “comprising” a certain element, this does not exclude the other element, but includes another element, unless specifically stated to the contrary. To do.
本出願の有機発光素子の有機物層は、単層構造からなってもよいが、２層以上の有機物層が積層された多層構造からなってもよい。例えば、本発明の有機発光素子の代表例として、有機発光素子は、有機物層として、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層などを含む構造を有することができる。しかし、有機発光素子の構造はこれに限定されず、より少数の有機層を含んでもよい。 The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but may also have a multilayer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. it can. However, the structure of the organic light emitting device is not limited to this, and may include a smaller number of organic layers.
本出願の一実施態様において、前記有機物層は、発光層を含み、前記発光層は、前記化合物を含む。 In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.
本出願の一実施態様において、前記有機物層は、正孔注入層または正孔輸送層を含み、前記正孔注入層または正孔輸送層は、前記化合物を含む。 In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
本出願の一実施態様において、前記有機物層は、電子輸送層または電子注入層を含み、前記電子輸送層または電子注入層は、前記化合物を含む。 In one embodiment of the present application, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
本出願の一実施態様において、前記有機物層は、電子輸送層、電子注入層、または電子注入または輸送を同時に行う層を含み、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、前記化合物を含む。 In one embodiment of the present application, the organic layer includes an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection or transport, and the electron injection layer, the electron transport layer, or simultaneously performs electron injection and transport. The layer comprises the compound.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、追加の化合物を含んでもよい。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layers carried out may comprise additional compounds.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、Ｎ型ドーパントを追加的に含んでもよい。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layers performed may additionally contain N-type dopants.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、金属錯体を追加的に含んでもよい。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layers carried out may additionally comprise metal complexes.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、アルカリ金属錯体を追加的に含んでもよい。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layers carried out may additionally comprise alkali metal complexes.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、リチウムキノレートを追加的に含んでもよい。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layer performed may additionally comprise lithium quinolate.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、本願の化合物とリチウムキノレートを１：９〜９：１の重量比で含むことができる。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layers carried out may comprise the compounds of the present application and lithium quinolate in a weight ratio of 1:9 to 9:1.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、本願の化合物とリチウムキノレートを４：６〜６：４の重量比で含むことができる。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layer to be performed can contain the compound of the present application and lithium quinolate in a weight ratio of 4:6 to 6:4.
本出願の一実施態様において、前記化合物は、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層に含まれ、前記電子注入層、電子輸送層、または電子注入および輸送を同時に行う層は、本願の化合物とリチウムキノレートを１：１の重量比で含むことができる。 In one embodiment of the present application, the compound is included in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and transport, and the electron injection layer, the electron transport layer, or the electron injection and transport simultaneously. The layers carried out can comprise the compound of the present application and lithium quinolate in a weight ratio of 1:1.
本出願の一実施態様において、前記有機物層の厚さは１Å〜１０００Åであり、より好ましくは１Å〜５００Åである。 In one embodiment of the present application, the thickness of the organic layer is 1Å to 1000Å, more preferably 1Å to 500Å.
本出願の一実施態様において、前記有機物層は、電子阻止層または正孔阻止層を含み、前記電子阻止層または正孔阻止層は、前記化合物を含む。 In one embodiment of the present application, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer contains the compound.
本出願の一実施態様において、前記有機発光素子は、第１電極と、前記第１電極に対向して備えられた第２電極と、前記第１電極と前記第２電極との間に備えられた発光層と、前記発光層と前記第１電極との間、または前記発光層と前記第２電極との間に備えられた２層以上の有機物層とを含み、前記２層以上の有機物層のうちの少なくとも１つは、前記化合物を含む。 In one embodiment of the present application, the organic light emitting device is provided with a first electrode, a second electrode provided to face the first electrode, and between the first electrode and the second electrode. A light emitting layer, and two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, the two or more organic material layers At least one of these comprises the compound.
本出願の一実施態様において、前記２層以上の有機物層は、電子輸送層、電子注入層、電子輸送および電子注入を同時に行う層、並びに正孔阻止層からなる群より２以上が選択されてもよい。 In one embodiment of the present application, the two or more organic material layers are two or more selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, and a hole blocking layer. Good.
本出願の一実施態様において、前記有機物層は、２層以上の電子輸送層を含み、前記２層以上の電子輸送層のうちの少なくとも１つは、前記化合物を含む。具体的には、本明細書の一実施態様において、前記化合物は、前記２層以上の電子輸送層のうちの１層に含まれてもよいし、それぞれの２層以上の電子輸送層に含まれてもよい。 In one embodiment of the present application, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be contained in one of the two or more electron transport layers, or may be contained in each of the two or more electron transport layers. You may
また、本出願の一実施態様において、前記化合物が前記それぞれの２層以上の電子輸送層に含まれる場合、前記化合物を除いた他の材料は、互いに同一でも異なっていてもよい。 Further, in one embodiment of the present application, when the compound is included in each of the two or more electron transport layers, the materials other than the compound may be the same or different from each other.
本出願の一実施態様において、前記有機物層は、前記化合物を含む有機物層のほか、アリールアミノ基、カルバゾリル基、またはベンゾカルバゾリル基を含む化合物を含む正孔注入層または正孔輸送層をさらに含む。 In one embodiment of the present application, the organic material layer includes, in addition to the organic material layer containing the compound, a hole injection layer or a hole transport layer containing a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group. Further includes.
もう一つの実施態様において、有機発光素子は、基板上に、陽極、１層以上の有機物層、および陰極が順次に積層された構造（ｎｏｒｍａｌ ｔｙｐｅ）の有機発光素子であってもよい。 In another embodiment, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
もう一つの実施態様において、有機発光素子は、基板上に、陰極、１層以上の有機物層、および陽極が順次に積層された逆方向構造（ｉｎｖｅｒｔｅｄ ｔｙｐｅ）の有機発光素子であってもよい。 In another embodiment, the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
例えば、本出願の一実施態様に係る有機発光素子の構造は、図１および図２に例示されている。 For example, the structure of the organic light emitting device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.
図１は、基板１、陽極２、発光層３、陰極４が順次に積層された有機発光素子の構造が例示されている。このような構造において、前記化合物は、前記発光層３に含まれてもよい。 FIG. 1 illustrates the structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 3.
図２は、基板１、陽極２、正孔注入層５、正孔輸送層６、発光層３、電子輸送層７、および陰極４が順次に積層された有機発光素子の構造が例示されている。このような構造において、前記化合物は、前記正孔注入層５、正孔輸送層６、発光層３、および電子輸送層７のうちの１層以上に含まれてもよい。 FIG. 2 illustrates the structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked. .. In such a structure, the compound may be contained in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
このような構造において、前記化合物は、前記正孔注入層、正孔輸送層、発光層、および電子輸送層のうちの１層以上に含まれてもよい。 In such a structure, the compound may be contained in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
本出願の有機発光素子は、有機物層のうちの１層以上が本出願の化合物、すなわち、前記化合物を含むことを除けば、当技術分野で知られている材料および方法で製造される。 The organic light emitting device of the present application is made of materials and methods known in the art, except that one or more of the organic layers comprises the compound of the present application, i.e., the compound.
前記有機発光素子が複数の有機物層を含む場合、前記有機物層は、同一の物質または異なる物質で形成される。 When the organic light emitting device includes a plurality of organic material layers, the organic material layers are formed of the same material or different materials.
本出願の有機発光素子は、有機物層のうちの１層以上が前記化合物、すなわち、前記化学式１で表される化合物を含むことを除けば、当技術分野で知られている材料および方法で製造される。 The organic light emitting device of the present application is manufactured using materials and methods known in the art, except that one or more of the organic material layers include the compound, that is, the compound represented by Chemical Formula 1. To be done.
例えば、本出願の有機発光素子は、基板上に第１電極、有機物層、および第２電極を順次に積層させることにより製造することができる。この時、スパッタリング法（ｓｐｕｔｔｅｒｉｎｇ）や電子ビーム蒸発法（ｅ−ｂｅａｍ ｅｖａｐｏｒａｔｉｏｎ）のようなＰＶＤ（Ｐｈｙｓｉｃａｌ Ｖａｐｏｒ Ｄｅｐｏｓｉｔｉｏｎ）方法を利用して、基板上に金属または導電性を有する金属酸化物、またはこれらの合金を蒸着させて陽極を形成し、その上に正孔注入層、正孔輸送層、発光層、および電子輸送層を含む有機物層を形成した後、その上に陰極として使用可能な物質を蒸着させることにより製造される。このような方法以外にも、基板上に、陰極物質から有機物層、陽極物質を順に蒸着させて有機発光素子を作ることができる。 For example, the organic light emitting device of the present application can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a PVD (Physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) is used to form a metal or a metal oxide having conductivity on the substrate. An alloy is vapor-deposited to form an anode, and then an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a substance usable as a cathode is vapor deposited thereon It is manufactured by In addition to this method, an organic light emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
また、前記化学式１の化合物は、有機発光素子の製造時、真空蒸着法のみならず、溶液塗布法によって有機物層に形成される。ここで、溶液塗布法とは、スピンコーティング、ディップコーティング、ドクターブレーディング、インクジェットプリンティング、スクリーンプリンティング、スプレー法、ロールコーティングなどを意味するが、これらにのみ限定されるものではない。 In addition, the compound of Chemical Formula 1 is formed in the organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
このような方法以外にも、基板上に、陰極物質から有機物層、陽極物質を順に蒸着させて有機発光素子を作ることもできる（国際特許出願公開第２００３／０１２８９０号）。ただし、製造方法がこれに限定されるものではない。 In addition to this method, an organic light emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited to this.
本出願の一実施態様において、前記第１電極は、陽極であり、前記第２電極は、陰極である。 In one embodiment of the present application, the first electrode is an anode and the second electrode is a cathode.
もう一つの実施態様において、前記第１電極は、陰極であり、前記第２電極は、陽極である。 In another embodiment, the first electrode is a cathode and the second electrode is an anode.
前記陽極物質としては、通常、有機物層に正孔注入が円滑となるように仕事関数の大きい物質が好ましい。本発明で使用可能な陽極物質の具体例としては、バナジウム、クロム、銅、亜鉛、金のような金属、またはこれらの合金；亜鉛酸化物、インジウム酸化物、インジウムスズ酸化物（ＩＴＯ）、インジウム亜鉛酸化物（ＩＺＯ）のような金属酸化物；ＺｎＯ：ＡｌまたはＳｎＯ２：Ｓｂのような金属と酸化物との組み合わせ；ポリ（３−メチルチオフェン）、ポリ［３，４−（エチレン−１，２−ジオキシ）チオフェン］（ＰＥＤＯＴ）、ポリピロールおよびポリアニリンのような導電性高分子などがあるが、これらにのみ限定されるものではない。 As the anode material, a material having a large work function is usually preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; zinc oxide, indium oxide, indium tin oxide (ITO), indium. metal oxides such as zinc oxide (IZO); ZnO: Al or SnO 2: combination of a metal oxide such as Sb; conductive poly (3-methylthiophene), poly [3,4- (ethylene -1 , 2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
前記陰極物質としては、通常、有機物層に電子注入が容易となるように仕事関数の小さい物質であることが好ましい。陰極物質の具体例としては、マグネシウム、カルシウム、ナトリウム、カリウム、チタン、インジウム、イットリウム、リチウム、ガドリニウム、アルミニウム、銀、スズおよび鉛のような金属、またはこれらの合金；ＬｉＦ／ＡｌまたはＬｉＯ２／Ａｌのような多層構造の物質などがあるが、これらにのみ限定されるものではない。 Generally, the cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF/Al or LiO 2 / There are materials such as Al having a multilayer structure, but the material is not limited to these.
前記正孔注入物質としては、電極から正孔を注入する層で、正孔注入物質としては、正孔を輸送する能力を有し、陽極からの正孔注入効果、発光層または発光材料に対して優れた正孔注入効果を有し、発光層で生成された励起子の電子注入層または電子注入材料への移動を防止し、また、薄膜形成能力の優れた化合物が好ましい。正孔注入物質のＨＯＭＯ（ｈｉｇｈｅｓｔ ｏｃｃｕｐｉｅｄ ｍｏｌｅｃｕｌａｒ ｏｒｂｉｔａｌ）が陽極物質の仕事関数と周辺有機物層のＨＯＭＯとの間であることが好ましい。正孔注入物質の具体例としては、金属ポルフィリン（ｐｏｒｐｈｙｒｉｎ）、オリゴチオフェン、アリールアミン系の有機物、ヘキサニトリルヘキサアザトリフェニレン系の有機物、キナクリドン（ｑｕｉｎａｃｒｉｄｏｎｅ）系の有機物、ペリレン（ｐｅｒｙｌｅｎｅ）系の有機物、アントラキノンおよびポリアニリンとポリチオフェン系の導電性高分子などがあるが、これらにのみ限定されるものではない。 The hole-injecting substance is a layer that injects holes from the electrode, and the hole-injecting substance has the ability to transport holes. A compound that has an excellent hole injection effect, prevents excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and has excellent thin film forming ability is preferable. It is preferable that the hole injection material has a HOMO (highest occupied molecular orbital) between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injecting substance include metal porphyrin, oligothiophene, arylamine-based organic substance, hexanitrile hexaazatriphenylene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, Examples of the conductive polymer include anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.
前記正孔輸送層は、正孔注入層から正孔を受け取って発光層まで正孔を輸送する層で、正孔輸送物質としては、陽極や正孔注入層から正孔輸送を受けて発光層に移しうる物質で、正孔に対する移動性の大きい物質が好適である。具体例としては、アリールアミン系の有機物、導電性高分子、および共役部分と非共役部分が共にあるブロック共重合体などがあるが、これらにのみ限定されるものではない。 The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. As the hole transport material, the hole transport material receives holes from the anode or the hole injection layer, and the light emitting layer. It is preferable to use a substance that has a high mobility for holes and is a substance that can be transferred to. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.
前記発光物質としては、正孔輸送層と電子輸送層から正孔と電子の輸送をそれぞれ受けて結合させることにより可視光線領域の光を発しうる物質であって、蛍光や燐光に対する量子効率の良い物質が好ましい。具体例としては、８−ヒドロキシ−キノリンアルミニウム錯体（Ａｌｑ３）；カルバゾール系化合物；二量体化スチリル（ｄｉｍｅｒｉｚｅｄ ｓｔｙｒｙｌ）化合物；ＢＡｌｑ；１０−ヒドロキシベンゾキノリン−金属化合物；ベンゾキサゾール、ベンズチアゾールおよびベンズイミダゾール系の化合物；ポリ（ｐ−フェニレンビニレン）（ＰＰＶ）系の高分子；スピロ（ｓｐｉｒｏ）化合物；ポリフルオレン、ルブレンなどがあるが、これらにのみ限定されるものではない。 The light emitting substance is a substance capable of emitting light in the visible light region by receiving holes and electrons from the hole transporting layer and the electron transporting layer and combining them, and has good quantum efficiency for fluorescence and phosphorescence. The substance is preferred. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compound; dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzoxazole, benzthiazole and Examples thereof include, but are not limited to, benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene and rubrene.
前記発光層は、ホスト材料およびドーパント材料を含むことができる。ホスト材料は、縮合芳香族環誘導体またはヘテロ環含有化合物などがある。具体的には、縮合芳香族環誘導体としては、アントラセン誘導体、ピレン誘導体、ナフタレン誘導体、ペンタセン誘導体、フェナントレン化合物、フルオランテン化合物などがあり、ヘテロ環含有化合物としては、ジベンゾフラン誘導体、ラダー型フラン化合物、ピリミジン誘導体などがあるが、これらに限定されない。 The light emitting layer may include a host material and a dopant material. The host material includes a fused aromatic ring derivative or a heterocycle-containing compound. Specifically, the fused aromatic ring derivative includes anthracene derivative, pyrene derivative, naphthalene derivative, pentacene derivative, phenanthrene compound, fluoranthene compound, and the like, and the heterocycle-containing compound includes dibenzofuran derivative, ladder-type furan compound, pyrimidine. Derivatives and the like, but are not limited to these.
前記電子輸送物質としては、電子注入層から電子を受け取って発光層まで電子を輸送する層で、電子輸送物質としては、陰極から電子注入をよく受けて発光層に移しうる物質であって、電子に対する移動性の大きい物質が好適である。具体例としては、８−ヒドロキシキノリンのＡｌ錯体；Ａｌｑ３を含む錯体；有機ラジカル化合物；ヒドロキシフラボン−金属錯体などがあるが、これらにのみ限定されるものではない。電子輸送層は、従来技術により使用されているような、任意の所望するカソード物質とともに用いることができる。特に、適切なカソード物質の例は、低い仕事関数を有し、アルミニウム層またはシルバー層が後に続く通常の物質である。具体的には、セシウム、バリウム、カルシウム、イッテルビウム、およびサマリウムであり、各場合、アルミニウム層またはシルバー層が後に続く。 The electron transporting material is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is a material that receives electron injection from the cathode and can be transferred to the light emitting layer. A substance having high mobility with respect to is preferable. Specific examples thereof include, but are not limited to, an 8-hydroxyquinoline Al complex; a complex containing Alq 3 ; an organic radical compound; a hydroxyflavone-metal complex. The electron transport layer can be used with any desired cathode material, such as those used in the prior art. In particular, examples of suitable cathode materials are the usual materials having a low work function, followed by an aluminum or silver layer. Specific examples are cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum or silver layer.
前記電子注入層は、電極から電子を注入する層で、電子を輸送する能力を有し、陰極からの電子注入効果、発光層または発光材料に対して優れた電子注入効果を有し、発光層で生成された励起子の正孔注入層への移動を防止し、また、薄膜形成能力の優れた化合物が好ましい。具体的には、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサゾール、オキサジアゾール、トリアゾール、イミダゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントロンなどとそれらの誘導体、金属錯体化合物および含窒素５員環誘導体などがあるが、これらに限定されない。 The electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, and an excellent electron injection effect for a light emitting layer or a light emitting material. Compounds which prevent the excitons generated in (2) from moving to the hole injection layer and have excellent thin film forming ability are preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and their derivatives, metal complex compounds and Examples include, but are not limited to, nitrogen-containing 5-membered ring derivatives.
前記金属錯体化合物としては、８−ヒドロキシキノリナトリチウム、ビス（８−ヒドロキシキノリナト）亜鉛、ビス（８−ヒドロキシキノリナト）銅、ビス（８−ヒドロキシキノリナト）マンガン、トリス（８−ヒドロキシキノリナト）アルミニウム、トリス（２−メチル−８−ヒドロキシキノリナト）アルミニウム、トリス（８−ヒドロキシキノリナト）ガリウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナト）ベリリウム、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナト）亜鉛、ビス（２−メチル−８−キノリナト）クロロガリウム、ビス（２−メチル−８−キノリナト）（ｏ−クレゾラート）ガリウム、ビス（２−メチル−８−キノリナト）（１−ナフトラート）アルミニウム、ビス（２−メチル−８−キノリナト）（２−ナフトラート）ガリウムなどがあるが、これらに限定されない。 Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinoline). Linato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]. Quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholate)aluminum , Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, and the like, but are not limited thereto.
前記正孔阻止層は、正孔の陰極到達を阻止する層で、一般的に、正孔注入層と同一の条件で形成される。具体的には、オキサジアゾール誘導体やトリアゾール誘導体、フェナントロリン誘導体、ＢＣＰ、アルミニウム錯体（ａｌｕｍｉｎｕｍ ｃｏｍｐｌｅｘ）などがあるが、これらに限定されない。 The hole blocking layer is a layer that blocks holes from reaching the cathode, and is generally formed under the same conditions as the hole injection layer. Specific examples thereof include, but are not limited to, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, BCP, and an aluminum complex.
本明細書に係る有機発光素子は、使用される材料によって、前面発光型、後面発光型、または両面発光型であってもよい。 The organic light emitting device according to the present specification may be a top emission type, a rear emission type, or a dual emission type, depending on the material used.
前記化学式１で表される化合物およびこれを含む有機発光素子の製造は、以下の実施例で具体的に説明する。しかし、下記の実施例は本明細書を例示するためのものであり、本明細書の範囲がこれらによって限定されるものではない。 The production of the compound represented by Formula 1 and the organic light emitting device including the same will be described in detail in the following examples. However, the following examples are provided to illustrate the present specification, and the scope of the present specification is not limited thereto.
＜製造例＞ <Production example>
＜製造例１＞化合物１の合成 <Production Example 1> Synthesis of compound 1
１）化合物１−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４５４ MS [M+H]+=454
２）化合物１−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝６３７ MS [M+H]+=637
３）化合物１の合成
ＭＳ［Ｍ＋Ｈ］＋＝６３７ MS [M+H]+=637
前記化合物１の合成確認資料を図３に示した。 The material for confirming the synthesis of Compound 1 is shown in FIG.
＜製造例２＞化合物２の合成
ＭＳ［Ｍ＋Ｈ］＋＝６３７ MS [M+H]+=637
前記化合物２の合成確認資料を図４に示した。 The material for confirming the synthesis of Compound 2 is shown in FIG.
＜製造例３＞化合物３の合成 <Production Example 3> Synthesis of compound 3
１）化合物３−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４９８ MS [M+H]+=498
２）化合物３−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５４６ MS [M+H]+=546
３）化合物３の合成
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物３の合成確認資料を図５に示した。 The material for confirming the synthesis of Compound 3 is shown in FIG.
＜製造例４＞化合物４の合成
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物４の合成確認資料を図６に示した。 The material for confirming the synthesis of Compound 4 is shown in FIG.
＜製造例５＞化合物５の合成 <Production Example 5> Synthesis of compound 5
１）化合物５−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５４６ MS [M+H]+=546
２）化合物５の合成
化合物３−Ｂの代わりに化合物５−Ｂを用い、（４−（１−ナフタレニル）フェニル）ボロン酸の代わりに（４−（２−ナフタレニル）フェニル）ボロン酸を用いたことを除き、化合物３と同様の方法で化合物５を製造した。
2) Synthesis of compound 5 Compound 5-B was used instead of compound 3-B, and (4-(2-naphthalenyl)phenyl)boronic acid was used instead of (4-(1-naphthalenyl)phenyl)boronic acid. Compound 5 was produced in the same manner as Compound 3 except for the above.
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物５の合成確認資料を図７に示した。 The material for confirming the synthesis of Compound 5 is shown in FIG.
＜製造例６＞化合物６の合成
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物６の合成確認資料を図８に示した。 The material for confirming the synthesis of Compound 6 is shown in FIG.
＜製造例７＞化合物７の合成
ＭＳ［Ｍ＋Ｈ］＋＝７３８ MS [M+H]+=738
＜製造例８＞化合物８の合成 <Production Example 8> Synthesis of compound 8
１）化合物８−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４５４ MS [M+H]+=454
２）化合物８−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝６３８ MS [M+H]+=638
３）化合物８の合成
ＭＳ［Ｍ＋Ｈ］＋＝７３８ MS [M+H]+=738
＜製造例９＞化合物９の合成
ＭＳ［Ｍ＋Ｈ］＋＝６３８ MS [M+H]+=638
前記化合物９の合成確認資料を図９に示した。 The material for confirming the synthesis of Compound 9 is shown in FIG.
＜製造例１０＞化合物１０の合成
ＭＳ［Ｍ＋Ｈ］＋＝６３８ MS [M+H]+=638
前記化合物１０の合成確認資料を図１０に示した。 The material for confirming the synthesis of Compound 10 is shown in FIG.
＜製造例１１＞化合物１１の合成 <Production Example 11> Synthesis of compound 11
１）化合物１１−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４９９ MS [M+H]+=499
２）化合物１１−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５４６ MS [M+H]+=546
３）化合物１１の合成
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物１１の合成確認資料を図１１に示した。 The material for confirming the synthesis of Compound 11 is shown in FIG.
＜製造例１２＞化合物１２の合成
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物１２の合成確認資料を図１２に示した。 The material for confirming the synthesis of Compound 12 is shown in FIG.
＜製造例１３＞化合物１３の合成 <Production Example 13> Synthesis of compound 13
１）化合物１３−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５４６ MS [M+H]+=546
２）化合物１３の合成
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
前記化合物１３の合成確認資料を図１３に示した。
＜製造例１４＞化合物１４の合成
<Production Example 14> Synthesis of compound 14
ＭＳ［Ｍ＋Ｈ］＋＝７１４ MS [M+H]+=714
＜製造例１６＞化合物１６の合成
１）化合物１６−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４６８ MS [M+H]+=468
２）化合物１６−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝６５２ MS [M+H]+=652
３）化合物１６の合成
ＭＳ［Ｍ＋Ｈ］＋＝６５２ MS [M+H]+=652
前記化合物１６の合成確認資料を図１４に示した。 The material for confirming the synthesis of Compound 16 is shown in FIG.
＜製造例１７＞化合物１７の合成
ＭＳ［Ｍ＋Ｈ］＋＝６５２ MS [M+H]+=652
前記化合物１７の合成確認資料を図１５に示した。 The material for confirming the synthesis of Compound 17 is shown in FIG.
＜製造例１８＞化合物１８の合成 <Production Example 18> Synthesis of compound 18
１）化合物１８−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝５１２ MS [M+H]+=512
２）化合物１８−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５６０ MS [M+H]+=560
３）化合物１８の合成
ＭＳ［Ｍ＋Ｈ］＋＝７２８ MS [M+H]+=728
＜製造例１９＞化合物１９の合成
ＭＳ［Ｍ＋Ｈ］＋＝７２８ MS [M+H]+=728
＜製造例２０＞化合物２０の合成 <Production Example 20> Synthesis of compound 20
１）化合物２０−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５６０ MS [M+H]+=560
２）化合物２０の合成
ＭＳ［Ｍ＋Ｈ］＋＝７２８ MS [M+H]+=728
前記化合物２０の合成確認資料を図１６に示した。 The material for confirming the synthesis of Compound 20 is shown in FIG.
＜製造例２１＞化合物２１の合成
ＭＳ［Ｍ＋Ｈ］＋＝７２８ MS [M+H]+=728
＜製造例２２＞化合物２２の合成
ＭＳ［Ｍ＋Ｈ］＋＝７５２ MS [M+H]+=752
前記化合物２２の合成確認資料を図１７に示した。 The material for confirming the synthesis of Compound 22 is shown in FIG.
＜製造例２３＞化合物２３の合成 <Production Example 23> Synthesis of compound 23
１）化合物２３−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４５４ MS [M+H]+=454
２）化合物２３−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝６３８ MS [M+H]+=638
３）化合物２３の合成
ＭＳ［Ｍ＋Ｈ］＋＝６３８ MS [M+H]+=638
＜製造例２４＞化合物２４の合成
ＭＳ［Ｍ＋Ｈ］＋＝６３８ MS [M+H]+=638
＜製造例２５＞化合物２５の合成
ＭＳ［Ｍ＋Ｈ］＋＝７３８ MS [M+H]+=738
＜製造例２６＞化合物２６の合成 <Production Example 26> Synthesis of compound 26
１）化合物２６−Ａの合成
ＭＳ［Ｍ＋Ｈ］＋＝４７２ MS [M+H]+=472
２）化合物２６−Ｂの合成
ＭＳ［Ｍ＋Ｈ］＋＝５２０ MS [M+H]+=520
３）化合物２６の合成
ＭＳ［Ｍ＋Ｈ］＋＝７３８ MS [M+H]+=738
＜実施例＞ <Example>
実施例１
ＩＴＯ（ｉｎｄｉｕｍ ｔｉｎ ｏｘｉｄｅ）が１，０００Åの厚さに薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波洗浄した。この時、洗剤としてはフィッシャー社（Ｆｉｓｃｈｅｒ Ｃｏ．）製品を使用し、蒸留水としてはミリポア社（Ｍｉｌｌｉｐｏｒｅ Ｃｏ．）製品のフィルタ（Ｆｉｌｔｅｒ）で２次濾過した蒸留水を使用した。ＩＴＯを３０分間洗浄した後、蒸留水で２回繰り返し超音波洗浄を１０分間進行させた。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をし乾燥させた後、プラズマ洗浄機に輸送させた。また、酸素プラズマを用いて前記基板を５分間洗浄した後、真空蒸着機に基板を輸送させた。
Example 1
A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, as the detergent, a product of Fischer Co. was used, and as the distilled water, distilled water secondarily filtered by a filter of a product of Millipore Co. was used. After cleaning ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water was completed, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, and the resultant was dried and then transported to a plasma cleaning machine. After cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum deposition machine.
こうして用意されたＩＴＯ透明電極上に、下記化合物［ＨＩ−Ａ］を６００Åの厚さに熱真空蒸着して正孔注入層を形成した。前記正孔注入層上に、下記化学式のヘキサニトリルヘキサアザトリフェニレン（ｈｅｘａａｚａｔｒｉｐｈｅｎｙｌｅｎｅ；ＨＡＴ）を５０Åおよび下記化合物［ＨＴ−Ａ］（６００Å）を順次に真空蒸着して正孔輸送層を形成した。 On the ITO transparent electrode thus prepared, the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, 50 Å of hexanitrile hexaazatriphenylene (HAT) represented by the following chemical formula and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited to form a hole transport layer.
次に、前記正孔輸送層上に、膜厚さ２００Åに下記化合物［ＢＨ］と［ＢＤ］を２５：１の重量比で真空蒸着して発光層を形成した。前記発光層上に、前記化合物１と［ＬｉＱ］（Ｌｉｔｈｉｕｍｑｕｉｎｏｌａｔｅ）を１：１の重量比で真空蒸着して、３５０Åの厚さに電子注入および輸送層を形成した。前記電子注入および輸送層上に、順次に、１０Åの厚さにリチウフルオライド（ＬｉＦ）と１，０００Åの厚さにアルミニウムを蒸着して陰極を形成した。 Next, the following compounds [BH] and [BD] were vacuum-deposited on the hole transport layer in a film thickness of 200Å in a weight ratio of 25:1 to form a light emitting layer. Compound 1 and [LiQ] (Lithium quinolate) were vacuum-deposited on the light emitting layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350Å. A cathode was formed on the electron injecting and transporting layer by sequentially depositing 10 liters of lithium fluoride (LiF) and 1,000 liters of aluminum.
前記過程で、有機物の蒸着速度は０．４〜０．９Å／ｓｅｃを維持し、陰極のリチウムフルオライドは０．３Å／ｓｅｃ、アルミニウムは２Å／ｓｅｃの蒸着速度を維持し、蒸着時の真空度は１×１０−７〜５×１０−８ｔｏｒｒを維持して、有機発光素子を作製した。
実施例２
前記実施例１における化合物１の代わりに化合物２を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 2
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 2 was used instead of Compound 1 in Example 1.
実施例３
前記実施例１における化合物１の代わりに化合物３を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 3
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 3 was used instead of Compound 1 in Example 1.
実施例４
前記実施例１における化合物１の代わりに化合物４を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 4
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 4 was used instead of Compound 1 in Example 1.
実施例５
前記実施例１における化合物１の代わりに化合物５を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 5
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 5 was used instead of Compound 1 in Example 1.
実施例６
前記実施例１における化合物１の代わりに化合物６を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 6
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 6 was used instead of Compound 1 in Example 1.
実施例７
前記実施例１における化合物１の代わりに化合物７を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 7
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 7 was used instead of Compound 1 in Example 1.
実施例８
前記実施例１における化合物１の代わりに化合物８を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 8
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 8 was used instead of Compound 1 in Example 1.
実施例９
前記実施例１における化合物１の代わりに化合物９を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 9
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 9 was used instead of Compound 1 in Example 1.
実施例１０
前記実施例１における化合物１の代わりに化合物１０を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 10
An organic light emitting device was produced in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in Example 1.
実施例１１
前記実施例１における化合物１の代わりに化合物１１を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 11
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 11 was used instead of Compound 1 in Example 1.
実施例１２
前記実施例１における化合物１の代わりに化合物１２を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 12
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 12 was used instead of Compound 1 in Example 1.
実施例１３
前記実施例１における化合物１の代わりに化合物１３を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 13
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 13 was used instead of Compound 1 in Example 1.
実施例１４
前記実施例１における化合物１の代わりに化合物１４を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 14
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 14 was used instead of Compound 1 in Example 1.
実施例１６
前記実施例１における化合物１の代わりに化合物１６を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 16
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 16 was used instead of Compound 1 in Example 1.
実施例１７
前記実施例１における化合物１の代わりに化合物１７を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 17
An organic light emitting device was produced in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in Example 1.
実施例１８
前記実施例１における化合物１の代わりに化合物１８を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 18
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 18 was used instead of Compound 1 in Example 1 above.
実施例１９
前記実施例１における化合物１の代わりに化合物１９を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 19
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 19 was used instead of Compound 1 in Example 1.
実施例２０
前記実施例１における化合物１の代わりに化合物２０を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 20
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 20 was used instead of Compound 1 in Example 1.
実施例２１
前記実施例１における化合物１の代わりに化合物２１を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 21
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 21 was used instead of Compound 1 in Example 1.
実施例２２
前記実施例１における化合物１の代わりに化合物２２を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 22
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 22 was used instead of Compound 1 in Example 1.
実施例２３
前記実施例１における化合物１の代わりに化合物２３を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 23
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 23 was used instead of Compound 1 in Example 1.
実施例２４
前記実施例１における化合物１の代わりに化合物２４を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 24
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 24 was used instead of Compound 1 in Example 1.
実施例２５
前記実施例１における化合物１の代わりに化合物２５を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 25
An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in Example 1.
実施例２６
前記実施例１における化合物１の代わりに化合物２６を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
Example 26
An organic light emitting device was produced in the same manner as in Example 1 except that Compound 26 was used instead of Compound 1 in Example 1.
比較例１
前記実施例１における化合物１の代わりに下記化合物ＥＴ１を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
An organic light emitting device was produced in the same manner as in Example 1 except that the following compound ET1 was used instead of the compound 1 in Example 1.
比較例２
前記実施例１における化合物１の代わりに下記化合物ＥＴ２を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
An organic light emitting device was produced in the same manner as in Example 1 except that the following compound ET2 was used instead of the compound 1 in Example 1.
比較例３
前記実施例１における化合物１の代わりに下記化合物ＥＴ３を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
An organic light emitting device was produced in the same manner as in Example 1 except that the following compound ET3 was used instead of the compound 1 in Example 1.
比較例４
前記実施例１における化合物１の代わりに下記化合物ＥＴ４を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
An organic light emitting device was produced in the same manner as in Example 1 except that the following compound ET4 was used instead of the compound 1 in Example 1.
比較例５
前記実施例１における化合物１の代わりに下記化合物ＥＴ５を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
An organic light emitting device was produced in the same manner as in Example 1 except that the following compound ET5 was used instead of the compound 1 in Example 1.
比較例６
前記実施例１における化合物１の代わりに下記化合物ＥＴ６を用いたことを除けば、実施例１と同様の方法で有機発光素子を作製した。
An organic light emitting device was produced in the same manner as in Example 1 except that the following compound ET6 was used instead of the compound 1 in Example 1.
前記実施例１〜１４、１６〜２６、および比較例１〜６の有機発光素子を１０ｍＡ／ｃｍ２の電流密度で駆動電圧と発光効率を測定し、２０ｍＡ／ｃｍ２の電流密度で初期輝度対比９０％になる時間（ＬＴ９０）を測定した。その結果を下記表１に示した。
前記表１の結果から、本明細書の一実施態様に係る化学式１で表される化合物は、有機発光素子の電子注入および電子輸送を同時に行える有機物層に使用可能であることを確認することができる。 From the results of Table 1, it can be confirmed that the compound represented by Chemical Formula 1 according to one embodiment of the present specification can be used in an organic material layer capable of simultaneously performing electron injection and electron transport in an organic light emitting device. it can.
特に、比較例２、６の化合物ＥＴ２、ＥＴ６は、本発明のＡｒ１およびＡｒ２が同一の化合物と比べて高い電圧、低い効率、低寿命を示すことを確認し、比較例３、４の化合物ＥＴ３、ＥＴ４は、本発明のＹの定義に含まれていない置換基を有する化合物で、実施例１〜１４、１６〜２６の化合物より高い電圧、低い効率、低寿命を示した。 In particular, the compounds ET2 and ET6 of Comparative Examples 2 and 6 were confirmed to have higher voltage, lower efficiency and shorter lifespan than the same compounds of Ar1 and Ar2 of the present invention, and the compounds ET3 of Comparative Examples 3 and 4 were confirmed. , ET4 are compounds having a substituent not included in the definition of Y of the present invention, and showed higher voltage, lower efficiency, and shorter lifetime than the compounds of Examples 1 to 14 and 16 to 26.
１：基板
２：陽極
３：発光層
４：陰極
５：正孔注入層
６：正孔輸送層
７：電子輸送層
1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole injection layer 6: Hole transport layer 7: Electron transport layer
Claims (10)
［化学式１］
Ｒは、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；シアノ基；置換もしくは非置換の炭素数１〜２０のアルキル基；置換もしくは非置換の炭素数３〜２０のシクロアルキル基；置換もしくは非置換の炭素数６〜２０の単環もしくは多環のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環のヘテロ環基であり、
Ａｒ１、Ａｒ２および−Ｌ−（Ｙ）ｎは、互いに異なり、
Ａｒ１およびＡｒ２は、互いに異なり、それぞれ独立に、非置換の炭素数６〜２０の単環もしくは多環のアリール基；または非置換の炭素数３〜２０の単環もしくは縮合環のヘテロ環基であり、
Ｌは、置換もしくは非置換の炭素数６〜２０の単環もしくは多環の３価〜６価のアリール基；または置換もしくは非置換の炭素数３〜２０の単環もしくは多環の３価〜６価のヘテロアリール基であり、
Ｙは、ナフチル基；フェナントレン基；ジメチルフルオレン基；アントラセン基；トリフェニレン基；ピレン基；テトラセン基；クリセン基；ペリレン基；またはフルオランテン基であり、
ｎは、２〜５の整数であり、複数のＹは、同一または異なる。 Compound represented by the following chemical formula 1:
[Chemical formula 1]
R's are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms. A group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,
Ar1, Ar2 and -L-(Y)n are different from each other,
Ar1 and Ar2 are different from each other and each independently represent an unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or an unsubstituted monocyclic or condensed heterocyclic group having 3 to 20 carbon atoms. Yes,
L represents a substituted or unsubstituted monocyclic or polycyclic trivalent to hexavalent aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic trivalent group having 3 to 20 carbon atoms to A hexavalent heteroaryl group,
Y is a naphthyl group; a phenanthrene group; a dimethylfluorene group; an anthracene group; a triphenylene group; a pyrene group; a tetracene group; a chrysene group; a perylene group; or a fluoranthene group,
n is an integer of 2 to 5, and a plurality of Ys are the same or different.
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| KR102050000B1 (en) | 2016-07-12 | 2019-11-28 | 삼성에스디아이 주식회사 | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
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| KR20200023984A (en) * | 2018-08-27 | 2020-03-06 | 삼성전자주식회사 | Heterocyclic compound and organic light emitting device including the same |
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| JP2019512499A (en) | 2019-05-16 |
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