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Equity
 12 Months Ended
Dec. 31, 2021
Equity [Abstract]  
Equity EQUITY
Dividend
Holders of the Company’s common stock are entitled to receive dividends when and if they are declared by the Company’s board of directors. The Company’s board of directors declared cash dividends of $0.08 per share during each of the first, second, third and fourth quarters of 2021, payments for which totaled $43.6 million. The Company’s board of directors declared cash dividends of $0.08 per share during each of the first, second, third and fourth quarters of 2020, payments for which totaled $43.5 million. During 2019, the Company’s board of directors declared cash dividends of $0.07 per share during each of the first and second quarters and $0.08 per share during each of the third and fourth quarters of 2019, payments for which totaled $40.8 million.
On January 19, 2022, the Company’s board of directors declared a quarterly cash dividend of $0.10 per share to be paid on February 23, 2022 to shareholders of record as of February 2, 2022.
Future dividend declarations, if any, as well as the record and payment dates for such dividends, are subject to the final determination of the Company’s board of directors. Furthermore, the credit agreements governing the New Credit Facilities contain restrictions that may limit our ability to pay dividends.
Share Repurchase Program
On December 14, 2020, the Company’s board of directors authorized a repurchase program, effective February 16, 2021, covering the repurchase of up to an aggregate of $125.0 million of the Company’s common stock, during a period of twelve months, in open market transactions and in accordance with one or more pre-arranged stock trading plans to be established in accordance with Rule 10b5-1 under the Securities Exchange Act of 1934, as amended. This repurchase program will expire pursuant to its terms on February 15, 2022. In connection with its proposed acquisition of CMC, the Company suspended this share repurchase program and does not anticipate authorizing a new program in 2022.
The Company repurchased $67.1 million, $44.6 million and $74.8 million of shares for the years ended December 31, 2021, 2020 and 2019, respectively.
The credit agreement governing the New Credit Facilities contains restrictions that may limit the Company’s ability to continue to repurchase shares.
2020 Stock Plan
In 2020, the Company’s board of directors and stockholders approved the Entegris, Inc. 2020 Stock Plan (the “2020 Stock Plan”). The 2020 Stock Plan replaced the Entegris, Inc. 2010 Stock Plan for future stock awards and stock option grants. The 2020 Stock Plan has a term of ten years and provides for the issuance of stock options and other share-based awards to selected employees, directors, and other individuals or entities that provide services to the Company or its affiliates. Under the 2020 Stock Plan, the board of directors or a committee selected by the board of directors will determine for each award, the term, price, number of shares, rate at which each award is exercisable and whether restrictions are imposed on the shares subject to the awards. The exercise price for option awards generally may not be less than the fair market value per share of the underlying common stock on the date granted. The 2020 Stock Plan provides that after December 31, 2019, any shares subject to stock awards that were awarded from the Company’s expired plans and that are forfeited, expired or otherwise terminated without issuance of shares will again be available for issuance under the 2020 Stock Plan.
For all plans, exclusive of the employee stock purchase plan, the Company had shares available for future grants of 8.7 million, 9.0 million, and 8.2 million shares at December 31, 2021, 2020 and 2019, respectively.
Stock Options
Stock option activity for the years ended December 31, 2021, 2020 and 2019 is summarized as follows:
 202120202019
(Shares in thousands)Number of
shares		Weighted
average
exercise
price		Number of
shares		Weighted
average
exercise
price		Number of
shares		Weighted
average
exercise
price
Options outstanding, beginning of year1,082 $33.38 1,575 $21.39 1,410 $18.22 
Granted167 98.11 216 55.72 293 33.33 
Exercised(592)27.32 (709)13.60 (128)13.89 
Expired or forfeited— — — — — — 
Options outstanding, end of year657 $55.32 1,082 $33.38 1,575 $21.39 
Options exercisable, end of year111 $34.54 426 $24.99 788 $15.75 
Options outstanding under the Company’s stock plans at December 31, 2021 are summarized as follows:
(Shares in thousands)Options outstandingOptions exercisable
Range of exercise pricesNumber
outstanding		Weighted
average
remaining life
in years		Weighted-
average
exercise
price		Number
exercisable		Weighted
average
exercise

price
$21.60 to $21.60
29 2.1 years$21.60 29 $21.60 
$31.10 to $31.10
101 3.1 years31.10 31 31.10 
$33.33 to $33.33
173 4.1 years33.33 27 33.33 
$55.72 to $55.72
187 5.1 years55.72 24 55.72 
$98.11 to $98.11
167 6.1 years98.11 — — 
657 4.7 years$55.32 111 $34.54 
The weighted average remaining contractual term for options outstanding and options exercisable for all plans at December 31, 2021 was 4.7 years and 3.6 years, respectively.
Under the stock plans, the total pre-tax intrinsic value of stock options exercised during the years ended December 31, 2021 and 2020 was $54.7 million and $36.4 million, respectively. The aggregate intrinsic value, which represents the total pre-tax intrinsic value based on the Company’s closing stock price of $138.58 at December 31, 2021, which theoretically could have been received by the option holders had all option holders exercised their options as of that date, was $54.7 million and $11.5 million for options outstanding and options exercisable, respectively.
Share-based payment awards in the form of stock option awards for 0.2 million, 0.2 million and 0.3 million shares were granted to employees during the years ended December 31, 2021, 2020 and 2019, respectively. Compensation expense is based on the grant date fair value. The awards vest annually over a period of four years and have a contractual term of 7 years. The Company estimates the fair value of stock options using the Black-Scholes valuation model. Key inputs and assumptions used to estimate the fair value of stock options include the grant price of the award, the expected option term, volatility of the Company’s stock, the risk-free rate and the Company’s dividend yield. Estimates of fair value are not intended to predict actual future events or the value ultimately realized by employees who receive equity awards, and subsequent events are not indicative of reasonableness of the original estimates of fair value made by the Company.
The fair value of each stock option grant was estimated at the date of grant using a Black-Scholes option pricing model. The following table presents the weighted-average assumptions used in the valuation and the resulting weighted-average fair value per option granted for the years ended December 31, 2021, 2020 and 2019:
Employee stock options:202120202019
Volatility38.0 %31.9 %31.6 %
Risk-free interest rate0.4 %1.4 %2.5 %
Dividend yield0.3 %0.6 %0.8 %
Expected life (years)4.64.34.1
Weighted average fair value per option$30.69 $14.83 $8.89 
A historical daily measurement of volatility is determined based on the expected life of the option granted. The risk-free interest rate is determined by reference to the yield on an outstanding U.S. Treasury note with a term equal to the expected life of the option granted. Expected life is determined by reference to the Company’s historical experience. The Company determines the dividend yield by dividing the expected annual dividend on the Company’s stock by the option exercise price.
Employee Stock Purchase Plan

The Company maintains the Entegris, Inc. Amended and Restated Employee Stock Purchase Plan (“ESPP”). The ESPP allows employees to elect, at six-month intervals, to contribute up to 10% of their compensation, subject to certain limitations, to purchase shares of the Company’s common stock at a discount of 15% from the fair market value on the first day or last day of each six-month period. The Company treats the ESPP as a compensatory plan. At December 31, 2021, 1.5 million shares remained available for issuance under the ESPP. Employees purchased 0.1 million, 0.2 million and 0.2 million shares, at a weighted-average price of $90.89, $46.58, and $28.67 during the years ended December 31, 2021, 2020 and 2019, respectively.
Restricted Stock Units
Restricted stock units are awards of common stock made under the Stock Plans that are subject to a risk of forfeiture if the awardee terminates employment with the Company prior to the lapse of the restrictions. The value of such restricted stock units is determined using the market price on the grant date. Compensation expense for restricted stock units is generally recognized using the straight-line single-option method. A summary of the Company’s restricted stock unit activity for the years ended December 31, 2021, 2020 and 2019 is presented in the following table:
202120202019
(Shares in thousands)
Number
of
shares		Weighted
average
grant date
fair value		Number
of
shares		Weighted
average
grant date
fair value		Number
of
shares		Weighted
average
grant date
fair value
Unvested, beginning of year1,083 $41.31 1,254 $27.48 1,519 $21.24 
Granted293 101.04 437 57.46 514 34.05 
Vested(439)35.58 (564)23.48 (679)18.89 
Forfeited(40)57.39 (44)35.86 (100)24.82 
Unvested, end of year897 62.69 1,083 41.31 1,254 27.48 

The weighted average remaining contractual term for unvested restricted shares at December 31, 2021 and 2020 was 1.1 years and 1.2 years, respectively.

During the years ended December 31, 2021, 2020 and 2019, the Company awarded performance-based restricted stock units for up to 0.1 million, 0.1 million and 0.1 million shares of common stock, respectively, to be issued upon the achievement of performance conditions under the Company’s stock plans to certain officers and other key employees. Compensation expense is based on the grant date fair value. The awards vest on the third anniversary of the award date. The Company estimates the fair value of the performance shares using a Monte Carlo simulation process.
As of December 31, 2021, the total compensation cost related to unvested stock options, performance-based restricted stock units and restricted stock unit awards not yet recognized was $5.8 million, $4.9 million and $37.9 million, respectively, and is expected to be recognized over the next 3.4 years on a weighted-average basis.
Valuation and Expense Information
The Company recognizes compensation expense for all share-based payment awards made to employees and directors based on their estimated fair values on the date of grant. Compensation expense is recognized using the straight-line attribution method to recognize share-based compensation over the service period of the award, with adjustments recorded for forfeitures as they occur. The following table summarizes the allocation of share-based compensation expense related to employee stock options, restricted stock awards, performance-based restricted stock awards and grants under the employee stock purchase plan for the years ended December 31, 2021, 2020 and 2019:
(In thousands)202120202019
Cost of sales$3,844 $1,463 $1,180 
Engineering, research and development expenses3,504 2,359 1,901 
Selling, general and administrative expenses22,536 19,098 16,548 
Share-based compensation expense29,884 22,920 19,629 
Tax benefit5,488 4,129 3,626 
Share-based compensation expense, net of tax$24,396 $18,791 $16,003