WO2020032424A1 - Élément électronique organique comprenant, en tant que matériau hôte, un mélange de différents types de composés, et dispositif électronique associé - Google Patents

Élément électronique organique comprenant, en tant que matériau hôte, un mélange de différents types de composés, et dispositif électronique associé Download PDF

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WO2020032424A1
WO2020032424A1 PCT/KR2019/008970 KR2019008970W WO2020032424A1 WO 2020032424 A1 WO2020032424 A1 WO 2020032424A1 KR 2019008970 W KR2019008970 W KR 2019008970W WO 2020032424 A1 WO2020032424 A1 WO 2020032424A1
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group
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ring
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박종광
조민지
김원삼
박정환
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덕산네오룩스 주식회사
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electronic device and an electronic device thereof, and more particularly, to an organic electronic device and an electronic device having improved driving voltage, luminous efficiency and lifetime by using a mixture of heterogeneous compounds as a host material.
  • a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of a host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • the present invention provides an electronic device including the organic electric element.
  • the driving voltage of the device can be lowered, luminous efficiency and lifetime Can improve.
  • heterocyclic group means a ring containing a heteroatom such as N, O, S, P or Si, instead of carbon forming a ring
  • heteroaryl group or “heteroarylene group”
  • aromatic ring such as a non-aromatic ring
  • fluorenyl group or “fluorenylene group” means a monovalent or divalent functional group in which R, R 'and R “are all hydrogen in the following structures, unless otherwise stated, and" Substituted fluorenyl group “or” substituted fluorenylene group “means that at least one of the substituents R, R ', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a carbon It includes the case of forming a compound by spying together.
  • the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are illustrated as examples of each symbol and substituents thereof may describe 'the name of the group reflecting the singer', but may be described as 'the parent compound name'.
  • the monovalent ⁇ group '' is phenanthryl and the divalent group may be described with the name of the group by dividing the mantissa, such as phenanthryl. Regardless, it may be described as the parent compound name 'phenanthrene'.
  • an organic electric device 100 may include a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110.
  • An organic material layer including the compound according to the present invention is included between the second electrodes 180.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, an electron injection layer 170, etc. sequentially stacked on the first electrode 120. .
  • at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like. It may also serve as a hole blocking layer.
  • the energy level and T 1 value between each organic layer by using a mixture of the various compounds represented by the formula (1), (2) and (3) as the host material of the light emitting layer, the energy level and T 1 value between each organic layer, the intrinsic properties (mobility, interface characteristics, etc.) ) To improve the lifespan and efficiency of organic electric devices.
  • the organic electric element according to an embodiment of the present invention may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
  • Ring A and Ring B are each independently an aromatic ring of C 6 -C 20 or a hetero ring of C 2 -C 20 .
  • the other one is a polycyclic ring in which two or more rings are condensed or adjacent R 1 are bonded to each other to form a ring.
  • the compound of formula 1 is a polycyclic compound in which at least six rings are fused.
  • the A ring may be substituted with one or more R 2
  • the B ring with one or more R 3 , and R 2 and R 3 may be each independently hydrogen; heavy hydrogen; halogen; Cyano group; C 6 ⁇ C 60 aryl group; Fluorenyl groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 60 ; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 ⁇ C 30 Alkoxy group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); and a plurality of R 2 and R 3 may be the same as or different from each other.
  • Ar 1 and Ar are fluorenyl groups, they may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, and the like.
  • R 'and R "are an aryl group it may be a C 6 -C 30 aryl group, more preferably a C 6 -C 12 aryl group, for example, phenyl, biphenyl, naphthyl and the like.
  • R 1 , R 2 , R 3 , Ar 1 , Ar, L 1 , L ', L, R a , R b , R', R ", and the ring formed by combining adjacent groups are each deuterium; halogen;
  • R 30 and R 31 are aryl groups, they may preferably be C 6 to C 30 aryl groups, more preferably C 6 to C 18 aryl groups such as phenyl, naphthyl, biphenyl, terphenyl and the like. .
  • L a is a single bond to each other independently; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 60 ; And a fused ring group of C 3 to C 60 aliphatic rings and C 6 to C 60 aromatic rings.
  • X 4 to X 6 are each independently C- (L-Ar ') or N, and at least one of X 4 to X 6 is N.
  • the ring comprising X 4 to X 6 may be a pyridine derivative, a pyrimidine derivative or a triazine derivative.
  • Ar 6 to Ar 8 is an aryl group, preferably an aryl group of C 6 to C 30 , more preferably an aryl group of C 6 to C 18 , such as phenyl, biphenyl, naphthyl, terphenyl, anthracene, Pyrene, phenanthrene, triphenylene and the like.
  • L is independently of each other a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 60 ; And a fused ring group of C 3 to C 60 aliphatic rings and C 6 to C 60 aromatic rings.
  • Z 1 to Z 48 are independently of each other C, C (R c ) or N.
  • the substituent R 1 or R 2 may be bonded to C, or may be bonded to L 2 or L 3 .
  • L a , R a and R b are the same as defined in Formula 2.
  • L 1 , L 4 to L 6 may be independently selected from the group consisting of the following Formulas b-1 to b-13.
  • R 4 to R 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 -C 20 aryl group; Fluorenyl groups; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 20 ; A fused ring group of an aliphatic ring of C 3 ⁇ C 20 and an aromatic ring of C 6 ⁇ C 20 ; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 ⁇ C 20 Alkoxy group; C 6 -C 20 aryloxy group; And -L a -N (R a ) (R b ); and adjacent groups can be bonded to each other to form a ring.
  • Y is independently of each other N- (L a -Ar a ), O, S or C (R d ) (R e ), Z 49 to Z 51 are independently of each other C, C (R c ) or N, At least one of Z 49 to Z 51 is N.
  • R c , R d and R e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 -C 20 aryl group; Fluorenyl groups; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 20 ; A fused ring group of an aliphatic ring of C 3 ⁇ C 20 and an aromatic ring of C 6 ⁇ C 20 ; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 ⁇ C 20 Alkoxy group; C 6 -C 20 aryloxy group; And -L a -N (R a ) (R b ); and R d and R e may be bonded to each other or adjacent R c may be bonded to each other to form a ring.
  • R d and R e are
  • Ar a is a C 6 ⁇ C 20 aryl group; Fluorenyl groups; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 20 ; And combinations thereof may be selected from the group.
  • L a , R a and R b are the same as defined in Formula 2.
  • Formula 1 may be represented by the following Formula 1-A or 1-B.
  • a ring, B ring, R 1 , L 1 , Ar 1 , X 1 , X 2 and a are the same as defined in formula (1).
  • Formula 1 may be represented by one of the following Formula 1-1 to Formula 1-42.
  • Formula 1 may be represented by one of the following Formula 1-C to Formula 1-J.
  • a ring, B ring, R 1 , R ', R ", L 1 , L, Ar 1 , Ar and a are the same as defined in the formula (1).
  • L 4 is a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 60 ; And a fused ring group of C 3 to C 60 aliphatic rings and C 6 to C 60 aromatic rings.
  • R 32 to R 34 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 -C 20 aryl group; Fluorenyl groups; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 20 ; A fused ring group of an aliphatic ring of C 3 ⁇ C 20 and an aromatic ring of C 6 ⁇ C 20 ; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 ⁇ C 20 Alkoxy group; C 6 -C 20 aryloxy group; And -L a -N (R a ) (R b ); It can be selected from the group consisting of, neighboring groups can combine with each other to form a ring.
  • r is an integer from 0 to 3
  • s is an integer from 0 to 5
  • t is an integer from 0 to 4
  • u is an integer from 0 to 4
  • each of R 32 each of which is an integer of 2 or more
  • each R 33 , each R 34 may be the same as or different from each other.
  • R c , R d and R e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 -C 20 aryl group; Fluorenyl groups; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 20 ; A fused ring group of an aliphatic ring of C 3 ⁇ C 20 and an aromatic ring of C 6 ⁇ C 20 ; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 ⁇ C 20 Alkoxy group; C 6 -C 20 aryloxy group; And -L a -N (R a ) (R b ); may be selected from the group consisting of.
  • R d and R e may be bonded to each other to form a ring, in which case a spiro compound is formed
  • each R 30 , each R 31 is the same as or different from each other, X 4 To X 8 , R 30 , R 31 and q are as defined in formula (2).
  • Chemical Formula 2 may be represented by the following Chemical Formula 2-G.
  • v and w are each an integer of 0 to 2
  • v + w is an integer of 1 or more
  • X 4 to X 8 are as defined in formula (2).
  • L 4 to L 6 , Ar 6 to Ar 8 are the same as defined in the formula (3).
  • X 7 and X 8 are independently of each other a single bond, N- (L a -Ar a ), O, S or C (R d ) (R e ), at least one of which is not a single bond.
  • Y 1 to Y 38 are independently of each other C, C (R c ) or N. It is C connected with the linking group L 4 among Y 1 to Y 38 .
  • Y 1 to Y 4 in Y 1 is L 4
  • Y 1 is a C
  • the other Y 2 to Y 4 are independently C (R c) or N with each other.
  • the ring is C 6 ⁇ C 60 Aromatic ring group; Fluorenyl groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 60 ; Or it may be a fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60.
  • R 13 is independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C 1 -C 20; An alkoxy group of C 1 -C 20 ; C 6 -C 20 aryloxy group; An alkyl group of C 1 -C 20 ; Alkenyl groups of C 2 -C 20 ; An alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; C 6 -C 20 aryl group substituted with deuterium; Fluorenyl groups; C 2 -C 20 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Aliphatic ring groups of C 3 -C 20 ; C 7 -C 20 ary
  • the ring is C 6 ⁇ C 60 Aromatic ring group; Fluorenyl groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 60 ; Or it may be a fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60.
  • Ar a is a C 6 ⁇ C 20 aryl group; Fluorenyl groups; C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C 3 ⁇ C 20 ; And combinations thereof may be selected from the group.
  • L a , R a , R b are the same as defined in Formula 2.
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the compound represented by Formula 2 may be one of the following compounds, but is not limited thereto.
  • the compound represented by Formula 3 may be one of the following compounds, but is not limited thereto.
  • the host is 40 to 80% by weight of the first compound represented by Formula 1, 10 to 30% by weight of the second compound represented by Formula 2 and 10 to 40% by weight of the third compound represented by Formula 3 Is done.
  • Sub 1-28b (40.93g, 105.11mmol), triphenylphosphine (68.92g, 262.77mmol), o -dichlorobenzene (526mL) was carried out in the same manner as the experimental method of Sub 1-1 to the product Sub 1-28 (15.03g, 40%).
  • Sub 1-103a (57.17g, 158.69mmol), 2-bromo-1-nitronaphthalene (40g, 158.69mmol), K 2 CO 3 (65.80g, 476.06mmol), Pd (PPh 3 ) 4 (5.50g, 4.76mmol ), THF (698ml) and water (349ml) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (47.61, 74%).
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • Compounds belonging to Sub 2 may be, but are not limited to, the following compounds.
  • Table 2 shows FD-MS values of the following compounds.
  • the compound represented by Chemical Formula 2 is synthesized by reacting Sub 3 and Sub 4 as in Scheme 4, but is not limited thereto.
  • 1,4-dibromo-9-phenyl-9H-carbazole (50.0 g, 125 mmol) was added to a round bottom flask and dissolved with toluene (500 mL), 2-chloroaniline (15.9 g, 125 mmol), Pd 2 (dba ) 3 (3.42 g, 3.74 mmol), P ( t -Bu) 3 (1.51 g, 7.48 mmol), NaO t -Bu (24.0 g, 249 mmol) were added and stirred at 120 ° C. After completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. The concentrate was then separated by silica gel column and recrystallized to give 43.0 g (yield: 77%) of product.
  • Sub3-a-13 (51.0 g, 170 mmol) and triphenylphosphine (111 g, 425 mmol) were used in the same manner as the synthesis of Sub3-a-3, to obtain 31.8 g (yield: 70%) of the product.
  • Compounds belonging to Sub 3 may be, but are not limited to, the following compounds.
  • Table 4 shows FD-MS values of the following compounds.
  • the compound represented by Formula 3 may be synthesized as in Scheme 6, but is not limited thereto.
  • Compounds belonging to Sub 5 may be the following compounds, but are not limited thereto, and Table 7 shows FD-MS values of the following compounds.
  • Sub 6 of Scheme 6 may be synthesized by the following Scheme 7, but is not limited thereto.
  • Compounds belonging to Sub 6 may be the following compounds, but are not limited thereto, and Table 8 shows FD-MS values of the following compounds.
  • a 4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as 2-TNATA) film is vacuum deposited on the ITO layer (anode) formed on the glass substrate, and the hole injection layer is 60 nm thick.
  • 2-TNATA 2-naphthyl (phenyl) amino] triphenylamine
  • NPB N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum
  • BAlq was vacuum-deposited on the light emitting layer to a thickness of 10 nm.
  • a hole blocking layer was formed, and Bis (10-hydroxybenzo [h] quinolinato) beryllium (hereinafter abbreviated as BeBq 2 ) was deposited to a thickness of 50 nm to form an electron transport layer.
  • BeBq 2 Bis (10-hydroxybenzo [h] quinolinato) beryllium
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that a mixture of compounds shown in Table 10 was used as a host material for the light emitting layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-101 was used alone (Comparative Example 1) or ref 4 compound was used alone (Comparative Example 2) as the host material of the emission layer. Produced.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using a mixture of Compound 1-101 and ref 4 as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that ref 3 compound, compound 2-34, and compound 3-99 were used as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that ref 5 compound, compound 2-34, and compound 3-99 were used as a host material of the emission layer.
  • the electroluminescence (EL) characteristics of the organic electroluminescent devices prepared according to Examples 1 to 12 and Comparative Examples 1 to 6 were measured by applying a forward bias DC voltage to PR-650 of photoresearch.
  • the T95 lifetime was measured using McScience's life measurement equipment at 2500 cd / m 2 standard brightness. The measurement results are shown in Table 10 below.
  • Comparative Examples 3 to 6 in which two or more compounds were mixed and used as a host rather than Comparative Example 1 and Comparative Example 2 using the compound of the present invention represented by Formula 1 and Comparative Compound ref 4 as a single host, respectively In the case of the device characteristics are improved.
  • Comparative Example 5 Comparative Example 6
  • the compounds belonging to the formulas (1), (2) and (3) of the present invention were mixed and used as a host. It can be seen that the devices of Examples 1 to 12 of the present invention significantly improve the efficiency and lifespan and lower the driving voltage.
  • the inventors of the present invention determine that each of the substances of Formula 1, Formula 2, and Formula 3, and mixtures thereof, have novel properties other than those of the substances on the basis of the above experimental results, The PL lifetime for these compounds was measured. As a result, in the case of the mixture of the present invention Formula 1, Formula 2, and Formula 3, it was confirmed that a new PL wavelength was formed, unlike the case of a single compound. It was confirmed that the decrease and disappearance time of each single substance represented by Formula 3 increased from about 60 times to as much as about 360 times.
  • the reason why the compound combinations such as the present invention is excellent is that due to the polycyclic compound of six or more rings represented by the formula (1), it is possible to improve not only electrons but also stability for holes, T1, and the like.
  • the compound represented by the formula (3) having a suitable energy band and high T1 is mixed, electron injection and transport ability is improved and stability is increased at the interface between the light emitting layer and the electron transport layer, and more holes move quickly and easily in the light emitting layer. Because it is.
  • the combination of the compounds represented by the formulas (1), (2) and (3), respectively, is electrochemically synergistic to improve the performance of the entire device.

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Abstract

La présente invention concerne : un élément électronique organique, qui utilise, en tant que matériau hôte d'une couche électroluminescente phosphorescente, un mélange comprenant un composé représenté par la formule chimique 1, un composé représenté par la formule chimique 2, et un composé représenté par la formule chimique 3 ; et un dispositif électronique associé, le mélange étant utilisé en tant que matériau hôte phosphorescent de telle sorte que la tension d'attaque d'un élément électronique organique peut être réduite et l'efficacité lumineuse ainsi que la durée de vie de celui-ci peuvent être améliorées.
PCT/KR2019/008970 2018-08-09 2019-07-19 Élément électronique organique comprenant, en tant que matériau hôte, un mélange de différents types de composés, et dispositif électronique associé WO2020032424A1 (fr)

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KR10-2018-0092970 2018-08-09

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KR20220013910A (ko) * 2020-07-27 2022-02-04 엘티소재주식회사 헤테로고리 화합물, 및 이를 포함하는 유기 발광 소자
KR102536903B1 (ko) * 2020-08-13 2023-05-26 엘티소재주식회사 헤테로고리 화합물, 이를 포함하는 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
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