JP2021100140A - 有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 - Google Patents
有機電気素子用化合物、これを用いた有機電気素子及びその電子装置 Download PDFInfo
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- JP2021100140A JP2021100140A JP2021036772A JP2021036772A JP2021100140A JP 2021100140 A JP2021100140 A JP 2021100140A JP 2021036772 A JP2021036772 A JP 2021036772A JP 2021036772 A JP2021036772 A JP 2021036772A JP 2021100140 A JP2021100140 A JP 2021100140A
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- 125000005842 heteroatom Chemical group 0.000 claims description 52
- 229910052760 oxygen Inorganic materials 0.000 claims description 52
- 229910052717 sulfur Inorganic materials 0.000 claims description 51
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 49
- 125000001931 aliphatic group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
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- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- XEMRLVBSKVCUDL-UHFFFAOYSA-N benzo[g]quinoxaline Chemical compound N1=CC=NC2=CC3=CC=CC=C3C=C21 XEMRLVBSKVCUDL-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- AJBBJCIPVQICEC-UHFFFAOYSA-N c(cc1)cc(c2c3)c1[s]c2ccc3-c1c(c(cccc2)c2[s]2)c2cc2ccccc12 Chemical compound c(cc1)cc(c2c3)c1[s]c2ccc3-c1c(c(cccc2)c2[s]2)c2cc2ccccc12 AJBBJCIPVQICEC-UHFFFAOYSA-N 0.000 description 1
- QJHHBGXACNUYHB-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)ccc1N(c(cc1)ccc1-c1ccccc1)c(cc1)ccc1-c(cc1)cc2c1-c1ccccc1C21c2ccccc2-c2c1cccc2 QJHHBGXACNUYHB-UHFFFAOYSA-N 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1Nc(cc1)ccc1-c1ccccc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1Nc(cc1)ccc1-c1ccccc1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- YEPVKHHZXQYSCO-UHFFFAOYSA-N c(cc1)ccc1Nc1cccc(-c(cc2)cc3c2c(cccc2)c2[n]3-c2ccccc2)c1 Chemical compound c(cc1)ccc1Nc1cccc(-c(cc2)cc3c2c(cccc2)c2[n]3-c2ccccc2)c1 YEPVKHHZXQYSCO-UHFFFAOYSA-N 0.000 description 1
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- JOFBTOVNZIUWPX-UHFFFAOYSA-N dibenzofuran-1-ylboronic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2B(O)O JOFBTOVNZIUWPX-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- MNXYJVWXMUBENA-UHFFFAOYSA-N dinaphthofuran Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)O3)C3=CC=C21 MNXYJVWXMUBENA-UHFFFAOYSA-N 0.000 description 1
- SYXXZXWLYNODHL-UHFFFAOYSA-N dinaphthothiophene Chemical group C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)S3)C3=CC=C21 SYXXZXWLYNODHL-UHFFFAOYSA-N 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ANCBHJKEYPZCTE-UHFFFAOYSA-N ethyl 5-carbamoyl-4-methyl-2-[(2,3,4,5,6-pentafluorobenzoyl)amino]thiophene-3-carboxylate Chemical compound CC1=C(C(N)=O)SC(NC(=O)C=2C(=C(F)C(F)=C(F)C=2F)F)=C1C(=O)OCC ANCBHJKEYPZCTE-UHFFFAOYSA-N 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- FTMRMQALUDDFQO-UHFFFAOYSA-N naphtho[2,3-b][1]benzofuran Chemical compound C1=CC=C2C=C3C4=CC=CC=C4OC3=CC2=C1 FTMRMQALUDDFQO-UHFFFAOYSA-N 0.000 description 1
- UWMISBRPSJFHIR-UHFFFAOYSA-N naphtho[2,3-b][1]benzothiole Chemical group C1=CC=C2C=C3C4=CC=CC=C4SC3=CC2=C1 UWMISBRPSJFHIR-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 159000000015 pyrido[4,3-d]pyrimidines Chemical class 0.000 description 1
- 150000008518 pyridopyrimidines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ZXVFTTRBWPOSLL-UHFFFAOYSA-N thieno[3,2-b][1]benzofuran Chemical group O1C2=CC=CC=C2C2=C1C=CS2 ZXVFTTRBWPOSLL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 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
- 238000001771 vacuum deposition Methods 0.000 description 1
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Abstract
Description
図1を参照すれば、本発明の一実施例に係る有機電気素子100は、基板上に形成された第1電極110、第2電極170及び第1電極110と第2電極170との間に形成された有機物層を含んでいる。
したがって、下記式4において、Y1、R11、R12、L4、L5、L6、Ar5、Ar6、cなどは、前記式2-Aで定義したものと同じであり、L21は式2又は式2-AのL’と同様な定義であり、R21とR22は、それぞれ式2又は式2-Aにおいて、Ra、Rbと同様な定義であり、dは0〜3の整数である。dが2以上の整数である場合には、R11は互いに同じであっても異なっていてもよく、隣接する基同士が互いに結合して環を形成していてもよい。
Sub1-9(56.7g、164.72mmol)にTHF(604mL)、Sub2-22(88.94g、197.66mmol)、Pd(PPh3)4(7.61g、6.59mmol)、K2CO3(68.30g、494.16mmol)、水(302mL)を添加し、前記1-6の合成法と同様の方法で反応を進行させて生成物81.17g(収率:73%)を得た。
ガラス基板に形成されたITO層(正極)上に4、4'、4"-トリス[2-ナフチル(フェニル)アミノ]トリフェニルアミン(以下、「2-TNATA」と略す)膜を真空蒸着して、60nmの厚さの正孔注入層を形成した後、4、4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(以下、「NPD」と略す)膜55nmの厚さで真空蒸着して正孔輸送層を形成した。
110:第1電極
120:正孔注入層
130:正孔輸送層
140:発光層
150:電子輸送層
160:電子注入層
170:第2電極
180:光効率改善層
210:バッファ層
220:発光補助層
320:第1正孔注入層
330:第1正孔輸送層
340:第1発光層
350:第1電子輸送層
360:第1電荷生成層
361:第2電荷生成層
420:第2正孔注入層
430:第2正孔注入層
440:第2発光層
450:第2電子輸送層
CGL:電荷生成層
ST1:第1スタック
ST2:第2スタック
Claims (10)
- 第1電極、第2電極及び前記第1電極と前記第2電極との間に形成された有機物層を含む有機電気素子において、
前記有機物層が、燐光性発光層を含み、前記燐光性発光層のホストは、下記式1で表される第1化合物と下記式2で表される第2化合物を含む有機電気素子:
前記式1と式2中、
X1はO又はSであり、
Ar1、Ar2、Ar4〜Ar6は、それぞれ独立に、C6-C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1種のヘテロ原子を含むC2-C60のヘテロ環基、C3-C60の脂肪族環基、C1-C30のアルキル基、C2-C30のアルケニル基、C2-C30のアルキニル基、C1-C30のアルコキシ基、並びにC6-C30のアリールオキシル基からなる群より選択され、
L1〜L6は、それぞれ独立に、単結合、C6−C60のアリーレン基、フルオレニレン基、O、N、S、Si及びPからなる群より選ばれる少なくとも1種のヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環基、並びにこれらの組み合わせからなる群より選択され、
R1は水素、重水素、ハロゲン、シアノ基、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPから選ばれる少なくとも1種のヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環基、C1−C50のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C30のアルコキシ基、C6−C30のアリールオキシル基、並びに−L’−N(Ra)(Rb)からなる群より選択され、隣接する基同士は、互いに結合して環を形成していてもよく、
aは0〜9の整数を表わし、aが2以上の整数である場合には、複数のR1は互いに同じであっても異なっていてもよく、
前記L’は単結合、C6−C60のアリーレン基、フルオレニレン基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環基、並びにこれらの組み合わせからなる群より選択され、
Ra及びRbは、それぞれ独立に、C6−C60のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C60のヘテロ環基、C3−C60の脂肪族環基、並びにこれらの組み合わせからなる群より選択され、
前記Ar1、Ar2、L1〜L6、R1、L'、Ra、Rb、及び隣接する基同士が互いに結合して形成された環は、それぞれ、重水素、ハロゲン、無置換の又はC1−C20のアルキル基若しくはC6−C20のアリール基で置換されたシラン基、シロキサン基、ホウ素基、ゲルマニウム基、シアノ基、ニトロ基、C1−C20のアルキルチオ基、C1−C20のアルコキシ基、C6−C20のアリールオキシル基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、C7−C20のアリールアルキル基、並びにC8−C20のアリールアルケニル基からなる群より選択された1種以上の置換基で更に置換されていてもよく、
Ar4〜Ar6は、それぞれ、重水素、ハロゲン、無置換の又はC1−C20のアルキル基若しくはC6−C20のアリール基で置換されたシラン基、シロキサン基、ホウ素基、ゲルマニウム基、シアノ基、ニトロ基、C1−C20のアルキルチオ基、C1−C20のアルコキシ基、C6−C20のアリールオキシル基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、C7−C20のアリールアルキル基、C8−C20のアリールアルケニル基、並びに−L’−N(Ra)(Rb)からなる群より選択された1種以上の置換基で更に置換されていてもよく、
但し、前記式2は下記式2-A〜2-Lのうちのいずれで表される化合物でもない:
前記式2-A〜2-Lにおいて、Ar5、Ar6、及びL4〜L6は、それぞれ式2におけるものと同様であり、
Y1〜Y3は、それぞれ独立に、O、S又はC(R’)(R”)であり、
R11〜R16、R’、及びR”は、それぞれ独立に、水素、重水素、ハロゲン、無置換の又はC1−C20のアルキル基若しくはC6−C20のアリール基で置換されたシラン基、シアノ基、ニトロ基、C1−C20のアルコキシ基、C6−C20のアリールオキシル基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、並びに−L’−N(Ra)(Rb)からなる群より選択され、隣接する基同士は、互いに結合して環を形成していてもよく、
bは0〜4の整数を表わし、bが2以上の整数である場合には、複数のR11それぞれ、複数のR13それぞれ、複数のR15それぞれは、互いに同じであっても異なっていてもよく、
cは0〜3の整数を表わし、cが2以上の整数である場合には、複数のR12それぞれ、複数のR14それぞれ、複数のR16それぞれは、互いに同じであっても異なっていてもよく、
前記L’、Ra及びRbは、式2におけるものと同様である。 - 前記L1〜L3のうちの少なくとも1つが、下記式b-1から式b-13のうちのいずれか1つで表される、請求項1に記載の有機電気素子:
前記式b-1から式b-13において、
R5〜R7は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C20のアルコキシ基、並びにC6−C30のアリールオキシル基からなる群より選択され、隣接する基同士は、互いに結合して環を形成していてもよく、
YはN-(La-Ara)、O、S又はC(R’)(R”)であり、
Z1〜Z3は、それぞれ独立に、C、C(R’)又はNであり、Z1〜Z3の中で少なくとも1つはNであり、
fは0〜6の整数を表わし、e、g、h、及びiは、それぞれ、0〜4の整数を表わし、j及びkは、それぞれ、0〜3の整数を表わし、lは0〜2の整数を表わし、mは0〜3の整数を表わし、これらのそれぞれが2以上の整数である場合には、複数のR5それぞれ、複数のR6それぞれ、複数のR7それぞれは、互いに同じであっても異なっていてもよく、
前記R’及びR”は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C20のアルコキシ基、C6−C30のアリールオキシル基、並びに−La−N(Ra)(Rb)からなる群より選択され、
C(R’)(R”)で、R’とR”同士は、互いに結合して環を形成していてもよく、C(R’)で、隣接するR’同士は、互いに結合して環を形成していてもよく、
前記Araは、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、並びにこれらの組み合わせからなる群より選択され、
前記Laは単結合、C6−C20のアリーレン基、フルオレニレン基、O、N、S、Si及びPからなる群より選ばれる少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、並びにこれらの組み合わせからなる群より選択され、
前記Ra及びRbは、それぞれ独立に、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、並びにこれらの組み合わせからなる群より選択される。 - 前記式1は下記式1-Aから式1-Gのうちのいずれか1つで表される、請求項1に記載の有機電気素子:
前記式1-Aから式1-Gにおいて、Ar1、Ar2、L1〜L3、X1、R1及びaは、それぞれ請求項1におけるものと同様であり、
X2及びX3は、それぞれ独立に、O又はSであり、
R4及びR5は、それぞれ独立に、水素、重水素、ハロゲン、シアノ基、ニトロ基、C6−C20のアリール基、フルオレニル基、O、N、S、Si及びPからなる群より選ばれた少なくとも1種のヘテロ原子を含むC2−C20のヘテロ環基、C3−C20の脂肪族環基、C1−C20のアルキル基、C2−C20のアルケニル基、C2−C20のアルキニル基、C1−C20のアルコキシ基、並びにC6−C30のアリールオキシル基からなる群より選択され、隣接する基同士は、互いに結合して環を形成していてもよく、
d’は0〜7の整数を表わし、e’は0〜6の整数を表わし、これらのそれぞれが2以上の整数である場合には、複数のR4それぞれ、複数のR5それぞれは、互いに同じであっても異なっていてもよい。 - 前記第1電極の両面のうち前記有機物層と接していない一面、又は前記第2電極の両面のうち上記有機物層と接していない一面に形成された光効率改善層を更に含む、請求項1に記載の有機電子素子。
- 前記有機物層は、前記第1電極上に順次形成された正孔輸送層、発光層、及び電子輸送層を含むスタック(stack)を複数含む、請求項1に記載の有機電子素子。
- 前記有機物層は、前記複数のスタック(stack)の間に形成された電荷生成層をさらに含む、請求項7に記載の有機電子素子。
- 請求項1に記載の有機電気素子を含むディスプレイ装置;及び
前記ディスプレイ装置を駆動する制御部を含む電子装置。 - 前記有機電気素子は、有機電気発光素子、有機太陽電池、有機感光体、有機トランジスタ、単色白色照明用素子、及び量子ドット(quantum dot)ディスプレイ用素子からなる群より選択される、請求項9に記載の電子装置。
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